Oh, this is so cute!
So charming.
[narrator] Colleen's been living in boyfriend Mike's 600 square-foot Chicago condo.
But it's time for something bigger.
So much counter space, modern appliances...
[narrator] Problem is, she's thinking of it as their home,
while he's prioritizing rental potential.
Having that second unit downstairs,
that can definitely handle a good portion of the mortgage.
[narrator] Will he and his friend, who's their agent,
get her on board the investment bandwagon?
Add an entrance, drywall, build a kitchen...
[Colleen] You guys and your house-hacking.
I just wanna be happy and comfy. [laughs]
[Jarret] Yeah.
-[doorbell rings] -[theme song playing]
[dynamic music playing]
A little chilly out here today.
Yeah. [laughs] I... It should be warmer out,
but at least some of the flowers are blooming.
Mike and I met six years ago
-I had a crush on her right away. [chuckles] -[laughs]
[Colleen] I'm an account manager, very organized. I love to plan.
I knew my whole life I was gonna be a business person,
so, um, you know, finance was a natural fit for me.
When we decided to move in together, I moved in to Mike's, uh, home.
It's very small. It's 600 square feet for the both of us.
It's been difficult. We both decided we're gonna buy a home together
for a little bit of a bigger space.
When it came to picking a real estate agent, we had to go with Jarret.
He's helped me pick out places in the past.
[Colleen] He's also our frie so he's very honest with us
and is like a great mentor just in this space.
I know you guys love talking about your investments and everything,
but this is my first time even purchasing a home.
I own two condos right now, and I look at real estate
as a great way to achieve financial freedom.
Mike and I look at things very differently.
He looks at things very logically, analytically.
I don't have that as much. I'm a very emotional person
Especially in terms of home.
-Multi-unit. -[Jarret] Okay.
Something where we could, you know, do short-term rental earn some extra income
and, you know, help pay off, uh, a little bit of our mortgage debt.
[Colleen] You guys and your house-hacking.
-I just wanna be happy and comfy. [laughs] -[Jarret] Yeah.
I'm definitely looking for single-family home.
I wanna make sure that at least we have two beds,
we have some good space and that the short-term renters would have
a completely different entrance.
-[Jarret] Yep. -I don't wanna see them, I don't wanna know about them.
Sure. Sure. You know I'm a little biased with, you know, short-term rentals.
-[Colleen] Yeah, I know. -Because I have a two-flat here that I rent out.
The one upstairs.
You could essentially do like a short-term rental with one side of it,
and then live in the other one.
And it would offset your costs.
The idea of a two-flat is great.
But you're getting the same amount of space as your guests
if we were to do a short-term rental.
I wanna be able to stretch out,
maybe buy some new furniture, host guests...
Also, I'm definitely looking for something with a little more character.
I want something more modern. Something that's easy to maintain over time.
What areas are you guys thinking about living in?
I just wanna be by public transportation.
We walk everywhere, and we try to take the train as much as we can.
-But then, we're also trying to keep it under about $500K. -[Jarret] Okay.
I know it's gonna be, you know, maybe tough to find something brand-new
in the price range we're looking at,
but we're willing to put in a little bit of work in terms of renovation.
-Right. -It's just, like, a little bit of a hard pill to swallow.
I don't know if we're ready for, like, a gut demo or anything like that.
Where our price point is at, we're probably gonna have to put in,
you know, some work in the renovation side.
We want a good house, good structure.
But I know she wants that, you know, perfect flooring,
the perfect paint, the, you know, perfect kitchen
where, uh, it's really difficult, especially in this market,
to find something like that.
I think we'll be able to get it done.
We just have to, you know, trust the process.
-We'll be able to find something that you love. -Mmm-hmm.
Something that's also great investment for Mike.
[upbeat music playing]
Two-flat, in West Town? $475,000?
Yeah. I mean, I... I love West Town.
And we're pretty close to the L.
But this curb appeal is just not great.
We are in West Town.
-Sure. -So West Town, two-flat, under $500,000.
-Not a lot of them. -[Colleen] Right.
-[Jarret] So let's keep an open mind. -[Colleen] Okay.
West Town has been an area that is highly sought after,
because of just being very central in Chicago, where transportation is close,
with buses, train systems, and the highway system.
And if they're renting out to short-term renters,
getting to festivals, concerts and other events around Chicago
would be very easy for them
[Jarret] The first floor uni is a two-bed, one-bath. Similar to the upstairs.
-Okay. -There's about 800 square feet down here.
[Mike] My favorite part about this property is the two-flat.
Having that second unit down there. You could probably fit six guests.
That's definitely a huge plus for me.
So I really like that aspect.
[Jarret] So, let's take a look upstairs. I'll lead the way.
[Colleen] Sure.
[dynamic music playing]
-[Jarret] Okay. Welcome, welcome. -[Colleen] Cool. Okay.
[Jarret] Okay, so we are in essentially the living room space.
They did leave some furniture.
[Colleen] I don't know. It's not that big.
[Mike] Really good natural light here.
-We'd wanna paint, we'd wanna do the trim. -Yep.
[Mike] I think maybe go black on the trim.
-Black? [laughs] -More modern.
Yeah, black's... Black's like a new thing.
Like, you'd definitely-- You could paint it black if you wanted to.
-No. -[Jarret] Okay.
That is not a thing.
[Jarret] All right. So, dining room.
[Colleen] The size is pretty good.
Do you guys do a lot of entertaining?
I mean, we couldn't in our last place because it was so small.
Having this space would be helpful for us.
I like planning. I like hosting.
I mean, I need that.
[Jarret] What are your thoughts on this kitchen? Come on in.
[Colleen] It's not very big
-There's a huge lack of counter space. -[Colleen sighs]
There's really nowhere you could put...
the food, you know.
-Where are you gonna put the cutting board? -[Jarret] Yeah.
What is this? This is so awkward.
What, am I supposed to climb in there?
[Mike] What do we got back there? [laughing]
-[Jarret] Yeah, you could climb on in. -Hello! [laughing]
So that's... That is essentially your pantry right now.
Jarret!
The pantry is the goofiest thing ever.
I do not understand.
We'd make an adjustment if we were to pick this place, for sure. [chuckles]
I'm definitely thinking
a gut rehab of this.
[Jarret] Okay. Probably like, $15 to $20K for this--
-[Colleen exclaims] -'Cause it's gonna be your kitchen, right?
-You're gonna live here, so... -No, I know. It sounds expensive.
-But, like, I don't like this in its... -[Jarret] Yeah.
...current form, so we'd have to.
[Jarret] All right. So now, we have our full bat
Everything is very dated. If we're meaning to do the kitchen,
I'd rather not fully redo a bathroom too.
[Jarret] We've got two bedrooms.
-[Colleen] Yeah. -[Jarret] So let's check ou the primary bedroom.
[Colleen] This is decent space.
And the... The closet space is fine. It's not bad.
[Mike] We're sharing a closet right now, so we can make it work.
Okay. Second bedroom.
[Colleen] Okay, this is tiny.
We can maybe do, like, a desk here.
I was looking for something a little bigger for a second bedroom.
-At least it has one. We don't need that now. -[Jarret] Right.
So there's actually an outdoor area that I want you guys to see.
-[Colleen] Okay. Oh! -[Jarret] This is one of two
-[Mike] Oh, this is great. - [Colleen] This is actua kind of cute.
I mean, I think it's nice just to be able to come out here, you know, eat breakfast.
-Yeah. -Out on the balcony. Get some fresh air.
[Colleen] Looks like there's an outdoor space down there too.
That's solid down there. I think our guests would really enjoy,
you know, just the ability to go outside like that.
-[Colleen] Yeah. -[Jarret] Sure.
[Mike] You know, we could put--
-Maybe a little, like-- -[Colleen] Clean it out, make it cute.
-Couches. Maybe, like, a grill. A table. -[Jarret] Yeah.
-[Mike] Yeah. -[Jarret] Yeah, sure. You could be cooking.
Colleen's down there, entertaining.
-You're yelling over the balcony... -Yeah. [chuckling]
[Jarret] "What do you need? Do you need a drink?"
-Yeah. -Yeah, just help us visualize it.
-[Jarret] Done, done. Easy. -Throw her a beer. [laughs]
[Jarret] Easy. So, let's walk back inside.
-You're good at your job, Jarret. -Thanks. I try, I try.
[chuckling]
[Jarret] So, what do you guy think about the, uh, two-fla
[Colleen] Looking at this space, it doesn't feel
a lot bigger than what we have now.
I mean, it's nice to have the two bedrooms.
I love the area.
But at the same time, this curb appeal... It's terrible.
You know, in terms of, like, the kitchen, the bathroom,
I know we're gonna have to put a lot of money into the place.
[Colleen] Mmm-hmm.
But one of the things I like about the place a lot is that, you know...
It's a two-flat.
Having that second unit downstairs, you know, we can definitely be able to
you know, do short-term rental downstairs.
Two bedrooms, one bath. What do you think we could get for that?
For in the warmer months, it could get up anywhere between $200 to $250 a night,
which is pretty substantial.
Wow. I thought it'd be lower than that, but that's pretty awesome.
-[Jarret] Yeah, it's pretty great, so... -Yeah.
And that could definitely handle, you know, a good portion of the mortgage.
I know Colleen isn't as focused on the short-term rental aspect
but if we could get a substantial portion
of that mortgage paid off each month,
it's really gonna give us a lot more flexibility in life.
I mean, I know you guys are both pro-two-flat, but... [laughing]
-Yeah. -I'm really looking for a single-family home, so...
-[Jarret] Sure. Sure. -Yeah. I'd love to see one.
And then just see kind of how that feels compared.
[upbeat music playing]
[Colleen] I'm super excited to see this.
[narrator] So now, Colleen and Mike are in the Chicago neighborhood
of Humboldt Park to see the type of house she wants, a single-family.
Oh, this is so cute!
Look at the scallops at the top. It's so charming.
[Mike] Really nice curb appeal.
I selected this property today because of the character that Colleen is going to love.
And also the feel of a home.
Michael potentially might not like it as much as Colleen,
but it also has the potential for a short-term rental
in the basement that is finished.
-Yeah. -We're kind of farther away.
You gotta take, like, a bus to a train to get to the city.
-[Colleen] Yeah. -[Mike] I could see it bein difficult for our guests.
You know, to wanna be able to travel around and...
-Yeah. -Move.
-[Colleen] That's true. But-- -You know, in terms of transport.
-Let's take a look. 'Cause I'm excited to see... -Yeah.
...a nice big space for us.
-It's really cool. -[Jarret] Sure.
[Colleen] A lot of historic like, Chicago charm.
-[Jarret] Yep. -Which I absolutely love.
[Jarret] This would be considered maybe your dining space.
Yeah. It would be nice to get a big table here.
Like, seat eight of my friends.
With the high ceilings, make it feel very, just like, inviting.
-[Jarret] Right. -That's our bedroom?
-That would be your bedroom. -Okay, let's see that.
-'Cause, right now, it looks pretty small. -[Jarret] Yeah.
Okay, let's check it out.
-Yes, it is. - [Colleen] Okay...
-The Chicago historic charm comes with its quirks. -[Jarret] Sure. Sure.
-[Colleen] Including the tiny bedroom. -[Jarret] Yep.
Would you put anything on that wall or this wall...
I just can't even visualize this here, 'cause we have our, like, nice night stands
on both sides, which we could never do here.
-It just doesn't make sense to me. -Okay.
-I was loving it, and now this is-- -[Jarret] Yep.
[Colleen] Just not great.
-[Jarret] So, here's your kitchen. -[Colleen] Okay!
-I mean, I love green on my shirts, but.. . [laug] -[Jarret] Sure, absolutely.
-[Colleen laughing] But not on the counters. -[Jarret] Okay, okay.
[Mike] One thing that I really like about this kitchen space
is that it's huge.
-[Jarret] Yep. -[Mike] Um...
[Colleen] Yeah.
[Mike] I mean, there's plent of counter space.
They finished this bathroom recently.
[Colleen] It's updated. But it's just really not my style.
I mean, we can make this wor 'cause we have before,
but it's just not a lot, and we're, you know, buying,
so I'd like to have a little more space.
-Okay. -[Colleen] But obviously, things can be renovated.
[Jarret] Second bedroom/office.
-[Colleen] So it'd have to b like, a long, skinny desk. - [Jarret] Yep.
Make it work.
Having that single-family home vibe is really important to me.
And I do love the older home
At the same time, my biggest concern about the house is
there's not a lot of space.
[Jarret] Check out this back area. I think you're gonna like it.
-[Colleen] Wow. This is huge -[Mike] Oh!
This is great!
Seeing this backyard is amazing. I can see us having a lot of friends over,
grilling outside...
There's so much we could do with this.
[Jarret] So that kind of, you know, leads us
into the separate, uh, unit down here.
-[door creaking] -For a short-term rental. Potential.
-Watch your head. The ceilings are lower. -[Colleen] Ooh. Yeah.
This is interesting. I feel like you guys look like giants...
-[Jarret] Yeah. -...in this space because it's so...
-Small. -Yeah, definitely, uh, was not built for a tall person.
-I mean, I think-- -[Colleen] Yeah.
My hair's touching that thing.
[Jarret] So this would be essentially kitchen space.
You have your washer, dryer hook-up there.
I mean, there's potential. You know, we could put an oven there.
-[Jarret] Yeah. -[Colleen] I mean--
Think about, like, the paint too.
[Colleen] Like, we wanna make this feel brighter.
-[Jarret] Yeah. -[Colleen] Obviously, we're in a basement.
But also, doing short-term rentals,
you don't need to give them everything.
-They're here for a few days. So just... Microwave, sink... -[Mike] That's true.
-Microwave. Fridge. Keep it simple. -[Jarret] Yep. Done.
So, this would be the bedroo
[Mike chuckling] This is bigger than the one upstairs
-Yeah. -Yeah.
[Jarret] This would be the bathroom.
[Colleen] This is so weird.
[chuckling] Just the basics in a bathroom.
[Mike] There's also no fan in the bathroom.
-[Jarret] That's true. -[Colleen] And like, we're in the basement.
-So it... Just the moisture. -[Jarret] Yeah.
Yeah. I could see that being an issue in the future.
-So that can be anywhere from $500 to $1,000. -Okay.
The finished basement, uh... You know, it's got its ups and downs.
I'm glad it's there.
You can pay off a portion of the mortgage.
You know, even half would be great.
But it needs a little bit of work. And, uh...
The ceilings are really short.
So I think that can definitely be an issue. [chuckles]
Uh, yeah... [chuckles] Maybe just ask for, like... short... [chuckles]
Short short renters. [chuckles]
[Jarret] Essentially, with renovating the downstairs,
you could probably bring in around $100 to $125 a night
If you didn't renovate it, and you just kept it at its current state,
it'd be around $75 a night.
-So-- -Ooh.
It's something to think about.
So what did you guys think about the home?
[Colleen] When you walk in, the high ceilings,
the historic charm of inside...
I just love it. The dining space is really great for hosting too.
[Mike] Great-sized kitchen. The bathroom is already nice
And having that potential short-term rental unit downstairs
is definitely a plus.
On the flipside of that, less revenue potential.
And also, it's small bedrooms and closets, though.
-[Mike] Yeah. -Like, I don't know if I could even picture myself there.
We have a lot of big furniture.
-[suspenseful music playing] -[narrator] Since no place has fully landed for them ye
Mike is hoping this more modern home will do the trick.
[Mike] This is amazing.
[upbeat music playing]
-[Colleen] Looks pretty big. -[Mike] Yeah.
Looks big. Looks really modern. I like that.
-Single-family home... -[Colleen] I'm intrigued.
Colleen, how are you?
-Good! How are you? -Good to see you.
-Good. -How nice to see you.
-Hey, Mike, how are you doing? -Good to see you.
[narrator] Mike and Colleen are in the area of Chicago called the Medical District
Since their agent thinks this neighborhood will appreciate.
[Jarret] We have a three-bedroom, two-and-a-half bath.
-[Colleen] Okay. -Basement could be...
Turned into a long-term rental or short-term rental.
-This would be your sitting formal area here. - [Colleen] Okay.
[Jarret] That which flows into, then, the dining room
I don't love the, like...
Wallpaper, the light fixture but those are things that we could easily change
The bones are good. I like how big the space is up here.
[Jarret] And then, what do you guys think about this kitchen?
-[Colleen] Wow! -[Mike] Looks great.
-[Colleen] I mean, it's pretty big. - [Jarret] Yep.
[Mike] This is amazing. There's so much counter spac Modern appliances.
-I mean, the kitchen isn't, like, my total style, per se. -Sure.
[Colleen] But the, like, space is great.
I would probably switch these out, maybe paint these.
[Jarret] To paint the cabinets, it would be $3K to $5K.
And then, the counter tops would probably be, like, $2K.
Yeah, and I think it's not something we urgently need to do.
But definitely something we can, you know, look into in the future.
[Colleen] Sure.
[dynamic music playing]
[Jarret] Come on out.
I was really hoping for a much bigger yard.
[Colleen laughs] I mean, the deck is fine.
We can definitely have, like, a table, utilize this space.
-There's space for being outdoors. -[Mike] Yeah.
[Colleen] I'm excited that there's an upstairs.
So you live downstairs, you sleep upstairs.
[Jarret] First bedroom.
[Colleen] Purple!
I mean, the space is great. The light's great.
It's not my style at all, but--
-Sure. -Easily paintable, obviously.
-[Jarret] Yep. -[Colleen] This is a nice si for an office.
[Jarret] So this could be, like, office number two.
[Colleen] I don't know about being, like, right next to each other.
-We're both loud. -[Jarret] Yeah. You're loud, Mike.
[Jarret] On the right-hand side, a full bathroom.
-[Mike chuckling] -[Colleen] No, this feels so... Just, like, dated.
[chuckles]
I mean, it's got a shower with a tub. I know that's gonna be great
in terms of, like, resale value.
-[Jarret] We're going from red to turquoise. -[Colleen laughs]
-[Jarret] Primary suite. -[Colleen] Oh, yeah. It's a pretty good size.
[Mike] Wow.
Oh, yeah. This is huge.
[Mike] Probably be able to p a king-sized bed here.
What are your thoughts on this bathroom?
-[Mike] I see that. -[Colleen] Yeah, the double vanity is clutch.
We have a single vanity now, and we make do, but having our own, it would be awesome.
I think you're gonna like this basement.
It's unfinished, but it's a lot of potential for short-term,
long-term rental.
[Jarret] Look at all of this space.
-[Colleen] Wow! -[Jarret] You can definitel do a lot in here.
What are you thinking? 'Cause I'm not 100% sure how this would work.
[Jarret] So, what we could essentially do here is add an entrance on the side,
drywall, build a kitchen, you know, put in some furniture.
And then, you could essentially have, like, a studio apartment down here.
[Mike] You have any idea what something like that might cost?
Maybe $20K to $30K for that whole project right there.
But for short term rentals, you could potentially get $125 to $150 a night.
[Colleen] I mean, that sounds good.
But I don't even know if guests for short-term rentals
would be even looking over here.
But with us being in the Medical District, you would have doctors,
nurses doing residencies,
being here for three to six months.
You could really get some really great income from this area.
-[Colleen] Right, like-- Yea -[Mike] Traveling nurses or.
-The medium term... -Yeah. People who come in and visit. Yeah.
-[Colleen] Whatever it is. -Exactly.
[Colleen] And for how long would it take from, like, start to finish,
getting this done?
Something in, conservatively, like four to six months.
[Colleen] The idea of it is interesting.
-Something to think about. -[Mike] Yeah. I mean, really nice space.
Big area here. Uh...
You know, I think we could make this really nice.
[dynamic music playing]
[Mike] I really like how modern it is.
And the spacious kitchen.
-[Jarret] Yep. -[Mike] That's a huge plus.
I mean, those are great, but then, thinking about downstairs...
Like, I wanna spend money for us up here.
It sounds like a lot downstairs too.
That's pretty concerning. And then, the location too.
I know it's good for guests, but for us, it's just not as practical.
Although I see this as more, you know, analytical point of view
I know the emotional side's really important too,
so we just have to find a place that we could really thrive in ourselves
and ideally a place where we can make money.
[upbeat music playing]
Looks like it's gonna be about 30, 33 minutes to get to my mom's right now.
Okay.
[narrator] Mike and Colleen are going to use this time to try to decide
on which house in Chicago they should choose.
[Mike] What do you think about the two-flat?
[Colleen] I love that it's in West Town.
I mean, we're over there already so often for, you know,
some of our favorite restaurants, and it's so close to the city.
So just being able to actually live there would be so awesome.
And the dining space is pretty nice too.
I could totally imagine our friends coming over ther
and us hosting.
[Mike] Yeah. Also having it two-bedroom, one bath,
definitely the most potentia income, you know, in terms of being able to rent it out
It's not a very charming curb appeal for our guests,
our friends, for us.
[Mike] The kitchen and the bathroom are also not the best we've seen.
We'd have to put a lot of work into that.
[Colleen] Well, what do you think about the Victorian, with the finished basement?
[Mike] Lowest price we've seen. Like that a lot
It's also got a really great back yard.
Yeah, and just the curb appeal is so charming.
Walking into... With the living room, dining room, high ceilings,
archways... [exclaims] I just love it.
I could definitely imagine us hosting.
On the other end though, the bedrooms.
Just tiny.
And then also, the ceilings and our unit would be...
So tall, [laughs] but thinking about the ceilings in the lower unit...
Like, you could barely walk down there.
And just the location is not prime.
And the potential income for a property like that is gonna be the lowest.
[Colleen] Well, what do you think about the modern home
with the unfinished basement
[Mike] I love the style of i Very modern.
A lot of space in the kitche
[Colleen] The space overall is just incredible. I can imagine us hosting.
-Also, just upstairs, three bed, two bath-- -Yeah.
-[Colleen] Which would be so luxurious. -[Mike] That would be great
Also, with the studio, I like the idea of being able to just really create a space
for our guests from scratch
But that location. I wouldn't even know where we're living.
-[Mike] Yeah. -[Colleen] It's just a little out there.
[Mike] Place didn't have the best outdoor space.
Also, in terms of time frame, you know, we could be looking at over six months
until we're earning rental income with something like that.
[dynamic music playing]
[doorbell rings]
We need to figure out how much space we have for the table.
I found something I like online, but I just don't know if it'll fit.
[Mike] We went with the two-flat.
[Colleen] The location's what got me.
I love this location.
And talking with Mike...
We kind of talked through upgrading the kitchen, bathroom,
kind of making it feel more like home for me,
but also maximizing the cash money coming in downstairs, so--
Technically.
[Colleen] I think we're gonn get the best of both worlds
once everything's done up here.
These floating shelves are gonna look great in the dining room.
I know. What are you thinking? Two, just like, right here?
-Yeah. -So, like, one here, One here.
The property was listed at $475,000.
So we came in, gave them in full $475,000.
[Colleen] The curb appeal isn't great.
We both know that. But I think that's why we go such a good deal on this.
We're really happy with what we landed.
The second bedroom is pretty small.
But the perk of having short-term rentals too
is you could save it for yourself, for your family.
Or, you know, people coming in town that are your friends.
All right, let's see what kind of space we have.
The downstairs unit, I think that's very suitabl for a short-term rental.
And now, we're just gonna d minor things to make it fee more at home.
I don't remember what the full dimensions are. What is it?
-Okay, this is 41.5 here. -Okay.
My plan is to just finish up the downstairs in the next couple weeks.
Make sure we could get some really good pictures down there,
and then list it online.
I feel like this could probably work.
And it's like, as long as people could walk through here,
and it doesn't come out so far, it should be fine.
-Okay. -I think it should fit. I'll just buy it.
[Mike] I think we made a great decision together.
We're gonna make a lot of new memories here as a couple.
We're gonna have a lot of fun.
[Colleen] I think it was the right decision for us.
[Mike] Yeah. I agree.