I have had to deal with this multiple times as the daughter and Niece trying to sell houses that weren’t  retail ready and it’s extremely stressful, especially if your dealing with a nursing home demanding financial proof that you can pay.

Stress-test: add 10% maintenance + proper landlord insurance + 1% rate shock.2) Financing playbook:HELOC: keeps your low first-mortgage rate, flexible, interest-only; great for the down payment on the new place.

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’d also stress test a couple bad scenarios like one big tenant leaves or rates stay higher longer and see if you still sleep at night after selling those units.What type of commercial is it and how many tenants.

When someone needs money upfront then definitely a scamThere are plenty of posts hear on BP how to spot a scam private hard money lender  Can't stress this enough! 

Otherwise they’re starting from scratch at a stressful time.For context, I’ve already started selling mine off (mentioned this in an earlier post), but that’s just my path.

Taxes, insurance, debt service, and closing costs don’t care which unit you live in.One thing I’d add that’s often missed: when house hacking, I always stress-test the deal assuming you move out in 1–2 years and it becomes a full rental.If it still meets your minimum DSCR and cash flow targets as a full rental, it’s usually a solid house hack.

When you systemize them, rent stays consistent and stress disappears.Here’s how we manage it efficiently across a growing portfolio:1.

I'm sure you understand the "burnout" that comes along with project management, so let me know if I can reduce some stress for you while learning more about your world!

DC is not the place to wing this or make emotional decisions.One important mindset shiftYour first goal is not max rent, it’s low stress and predictability, especially since you’ll be living on the property.