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?

I need to have it done by the end of the year and I am starting to stress! 

Hi Ed, I wouldn't stress too much on changes in the central Florida market unless your getting condos. 

I say “evil” because when you’re not organized, getting there feels painful — but once you’ve got systems in place, maintaining them is so much easier than trying to dig yourself out later.There are all kinds of levels of disorganization, but one thing’s certain: rental property management runs a whole lot smoother (and feels way less stressful) once you’ve got structure and processes dialed in.I see the same thing with the investors I work with — once their systems and books are organized, everything else in their business starts to run more efficiently.

I have yet to find an easy button for organizing transactions and subsequent reporting, so I use a bookkeeper.

DSCR is still a solid way to scale, but it’s not quite the “easy button” it was a couple years ago.

If you want, I can share the analyzer I use to quickly stress-test deals so you’ll know what to expect before making offers. 

I can't stress enough - if something doesn't feel right, you are within your right to stop and get an explanation or get another professional.

How do you handle stress during peak periods?

Rising rates, affordability stress, and valuations detached from fundamentals are flashing red.I’ve been through cycles before.