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All Forum Posts by: Luke Stewart

Luke Stewart has started 10 posts and replied 108 times.

Post: Downtown Chicago Midterm Rentals

Luke StewartPosted
  • Investor
  • Posts 109
  • Votes 148
Quote from @Tom Casey:

Hey Luke!

So the good news is that there are currently two full-amenity condo buildings in/near downtown Chicago in prime A+ Class neighborhoods that allow short-term rentals: 545 N Dearborn and 30 E Huron. However, both associations have a 30-day minimum for all lease agreements.

Unfortunately, the bad news is that there really aren't any other buildings that I know of where the association allows short-term leases. I have done quite a bit of digging and I've been told by multiple agents that these are the only two that don't have rules against STR.

If you're serious about going this route, I believe that these two buildings would be a good place to start.

Also, if you're not completely set on the buildings being full amenity, I agree with @Michael K. that you can find some multi-unit gems in great neighborhoods and operate them as STR buildings. Just be wary that technically, according to Chicago's Airbnb ordinance, you can only operate 25% of the units in your building as Airbnbs. I heard this on Straight Up Chicago podcast episode 143 about rules for STRs in Chicago. Here's a link to that episode if you're interested: https://www.straightupchicagoi... 

I think that overall, multi-unit buildings will be your best bet if you don't want to risk getting in trouble with condo associations. 

However, if you don't mind taking on that risk, you can also run numbers for condo units so that they still work as regular rentals. Then if the association cracks down, you'll have a backup plan where you still at least break even on PITIA.

Hope that helps!


 Tom,

This is great information, thank you. I am definitely focused on 1 month or more rentals, I love the mid rental approach, aiming at people waiting to buy home, people in the city for work, so in that regard it definitely makes the HOA laws more flexible. I am not set on full amenities but I do find that my Denver spot rents constantly and I believe a lot of that is due to the fact that its a one stop shop for people coming for work. Its nice to have a gym when youre only in town for 1-3 months. Thanks for everything you added here, this is super super helpful!

Post: Downtown Chicago Midterm Rentals

Luke StewartPosted
  • Investor
  • Posts 109
  • Votes 148
Quote from @Michael K.:
Quote from @Luke Stewart:

I am looking to buy a condo in the city using a second home loan. I know all the second home loan requirements so no need to hash that out here. I am more interested in people who do midterm rentals, anything over 1 month....

I know some people who rent to travel nurses/techs etc, I think its a great business idea. If you are in the industry then you already have the connections. My wife is also in healthcare so we've considered going that route too. Just be careful that the condo building you are buying into allows for short-term rentals (or any rentals for that matter). That's sort of the catch, the larger the building and the more amenities it has, the more rules you will run into. 2-3 story walk-ups in nice neighborhoods could be a good place to start, lower HOA fees too.


 Thanks Michael,

I try and skip the STR rules by doing over 1 month, however if I had the option I would definitely fill gaps that way. Good to know about bigger buildings and more amenities having more rules, that makes total sense to protect the full time residents. I love the midterm rental and its how I rent my home in Denver. My family is in Chicago so I am curious to buy a place that I would live in when in town. But I know Chicago winters too well, and the last thing I want is to calculate cash flow and returns on summer rent to have it turn negative come January. Thanks for the insight!

Post: Downtown Chicago Midterm Rentals

Luke StewartPosted
  • Investor
  • Posts 109
  • Votes 148

I am looking to buy a condo in the city using a second home loan. I know all the second home loan requirements so no need to hash that out here. I am more interested in people who do midterm rentals, anything over 1 month, fully furnished. I grew up here and when I came to the city as a travel nurse this summer, the month to month furnished rentals were outrageously expensive, $4000-$5000 a month easily to be in a nice building anywhere in River North, Gold Coast, Lincoln Park, West Loop etc. I have done multiple calculations and it seems like that market has great cashflow... in the summer. Does anyone have experience to share about this specific rental in the city throughout the year? Pros and cons. Is gym or parking a huge plus? I always view midterm renters people who want all the amenities. It seems like a great market for that despite the property taxes. Any advice is greatly appreciated!

I accept pets, I know that in my area in Denver I can charge more per month that I would be able to. I also just do mid term rentals, longest so far being 5 months. So I can have the place really cleaned well in between each renter. I don't think the weight is as important as the age and breed. Cats will do more damage than the average dog in my opinion. Just accept that while you'll take more in each month, you will have to replace carpet, couches, etc, sooner. Also if you get a bad renter, it could be hell. Big security deposit is KEY!

I am a travel nurse myself, I would say the demand has dropped a little bit since March but it has picked back up. I am not sure why its picked back up besides the continual nursing shortage that never gets better. My best hypothesis is that nurses like traveling and not being a "staff" nurse that involves the politics of being an employee. There were definitely higher paying jobs last year than now, but the pay is still well over double that of a staff nurse and that will keep people traveling. 

With my rental, I list on furnished finder but also put it on airbnb for greater than 1 month rentals and have had no problem keeping it rented. My place is also in Denver which has always been a hot spot for travel nurses. 

I do think that if you are hoping for travel nurses in more small town/suburbs, I think that demand will drop more. During C19, the pay in places like Fargo, ND and these small rural hospitals that were severely understaffed were paying outrageous money, some 7-8k a week. That will not continue as hospitals cant sustain it. But in "fun, exciting" locations, travel nursing will continue. Just my thinking as a current travel nurse and feeling out the market.

@Rosalie Borja I appreciate your thoughts on this. I am leaning towards keeping my primary but I also am going to discuss this with my realtor and lender to see what they are thinking. I am currently out of state for work and I also am a little uneasy about selling and buying all at once while out of state. I see them both as good moves but I also know that the upgrade path comes with more risk simply because of the higher mortgage payment. Learning to manage risk is key, and I feel like getting my second home complete seems like a smart move before I jump into this. That being said, I'm gonna talk to my team and consider all options. Thanks for your response!

@Ryan Williams I appreciate your response. I have an excellent first loan so it makes me want to keep my primary residence. Especially since I know what it can produce in terms of cashflow. I am in the process of buying a "second home" loan and am really focused on that to be done by the end of the year but started looking into rolling the equity and wanted some other opinions. I am new to this and I keep saying cash flow, cash flow, cash flow and that will make buying a nicer property down the road that much easier.

I guess when I say "market moving", I am more concerned with housing prices continuing to rise as I do not see a dip coming to Denver. I just realized that I could upgrade my property and got nervous that if I decided not to do it then in a year I may not be able to afford the properties that I could right now. Just more fear than anything. But I keep reminding me my first mortgage is so strong that I really shouldn't touch it.

I think I am gonna give it time, focus on the second home loan on a condo in Chicago and then come back to it in a year maybe with a Heloc.

I am stuck at a what to do, looking for some unbiased opinions. I have a 3 story townhome in Denver worth $440,000 with $250,000 left on my loan (2.5%, 15year. $2300/m total payment). I am currently mid-term renting the condo while out of state for work bringing in $3000 a month ($500cf/m after utilities). I am considering upgrading to a nicer 3 story townhome in the 600-700k range. Ideally paying 3k-3.5k/m mortage on 30y @ 5.8% with the intention to refinance down the road if rates improve. I believe I could still rent it out midterm for 4k a month, basically being the same cash flow, but a much different loan. It is still my primary and I live there sporadically, will be back full time in less than a year. 

My question is does this make sense to do now or should I wait to see how the market moves. I believe that it makes sense to make the move now regardless of the market since I can cover the expenses with my income and down the road in Denver this should be a $1M property. I have worked out all the numbers I just am looking for any insight or opinions. I am new to real estate investing so trying to learn and manage risk! Love the community, thanks for your help!