Platforms to use:Furnished Finder is a big one for corporate and traveling professionals (nurses, consultants, tech workers).Airbnb/VRBO can work too, but corporate folks usually prefer something more “stable” than nightly.

Does someone work night shift , who gets the driveway to park ? 

There are too many $99/night bottom feeders here.

Use conservative financing that protects sleep at night: conventional or DSCR with solid reserves, or buy with seller/private money then refi once stabilized.

One is tech professional who works nights.

I just worry if something happens late at night and I need to act fast, I don't want to fully rely on the first google search result.

Back in 2010 banks wanted to get rid of their REO before the end of the year, later it was short sales, today it's just regular sellers that are seeing the leaves turn, we may get the first night frost this weekend, showings are slowing down more and more every week - seller anxietly is growing.If you look at the chart you can see an over 10% swing betweeen highs and lows.

Maybe drive them on afternoon weekday afternoon and a weekend night. 

As they struggle to come up with the money to pay your LTR, they'll start dropping minimum night stays and letting people use it as a party house, then after a month or two or three when they figure out they're making nothing they'll slink off into the night and you'll have the fun of repairing your house. 

The demand is usually steady year-round in Chicago for that group.That said, here’s how I’d weigh it:If you go MTR:You’ll need to furnish it properly — not fancy, but turnkey: queen bed in each room, blackout curtains, comfy couch, smart TV, solid Wi-Fi, a stocked kitchen (pots/pans, utensils, coffee maker, toaster), and a simple desk setup.Expect about $4K–$6K upfront to get it guest-ready if you’re starting from scratch.Cleaning and turnover management can be automated (Turno app or a local cleaner), but there’s still some coordination involved.Since you’re near a hospital, list on both Furnished Finder and Airbnb (30+ night stays) — that combo usually keeps you booked.If you go LTR instead:You’ll save yourself the time and mental load of setting up a new system while adjusting to newborn life.Even if the rent’s lower, you’ll get steady income and less stress, which might be worth it right now.Winter leasing in Chicago:Yeah, it’s slower — especially December through February — but MTRs tied to hospitals stay active because medical contracts don’t follow the same seasonality.If this were me?