I've posted in this forum before on this subject (Chicago Mid-Term Rentals). I'll just paste my previous post below (with a few updates):
I'm all in on my Chicago-area MTR operation. I now have 6 buildings with 39 total units. I operate 35 of the units as Mid-Term rentals in suburban Chicago. I own all of the buildings except two (a 6- unit building and a 2-flat). The 6-unit building I previously owned - I sold it and leased back the apartments from the new owner (Arbitrage/Master Lease). The 2-flat I run on the arbitrage model. I have a 2-flat under contract. The other buildings are a 10-unit, a 9-unit, and two 6-unit buildings.
I generally try to get 2X the market rent - and I get close to that amount most of the time. I run about 80% occupancy but much of the time I am 100% occupied. There are a few slower months that bring my overall annual occupancy down to 80-85%. Since we are getting 2x market rent, my cash flow is many multiples of what I would get using a typical LTR tenant.
We only offer extended stays of 30 nights or greater. These are not full-amenity buildings. These are small vintage buildings but we have fully renovated and updated all of the units and common areas. We spend a lot of time furnishing and styling these units. They are decorated in a very stylish manner. We are generally trying to attract an upscale, professional guest. Some of the units have an in-unit washer and dryer (or we have a laundry room in the building). Most of the units have a dishwasher. On a case-by-case basis we allow pets. Each comes with 1 parking space. We have mostly have 1 and 2 bedroom apartment. My 2-flats are 3-bedroom units (which are much in demand from "families" needing temporary furnished housing).
Note: These are suburban buildings but in highly desirable towns with close proximity to downtown Chicago. So there is plenty to do in the suburbs itself. In other words, these are GREAT locations.
I used a traditional bank to finance the purchase of each of these buildings - using a traditional commercial real estate mortgage. The bank underwrites the loans using a traditional "market" rent analysis for the property. In other words, when purchasing they don't really consider my projections for the enhanced (very enhanced) cash flow from the furnished operation (although they understand this business and I provide detailed financial information to them). For the most part, I've self-financed the renovations and furnishings of the apartments. Those capital expenditures are SIGNIFICANT at this scale.
This is a completely self-managed operation (we don't use property management firm). I have a property manager, cleaning, and maintenance people. We have our own laundry facility. This is a COMPLICATED business to run at this scale. Cleaning and maintenance pose significant challenges. Overall revenue is over $1M and scaling up as we bring more units into the program.
I started with a single STR (as an experiment) in a six-unit building that I owned. I've scaled up from there - eventually converting my furnished business from STRs to MTRs and converting most of my units from long-term tenants to MTRs.