What you learn here, plus the tax benefits and equity, makes it easier and less stressful to take on your next investment.

It also helped me keep personal and investment money separate, which reduces stress.

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?

Verify rents with a local PM, stress‑test at higher rates and conservative vacancy, and only buy if it cash flows without short‑term rental income.

I’ve been hearing a lot about turnkey properties — homes that are already renovated, tenant-occupied, and ready to cash flow from day one.On paper, they sound like a stress-free way to get started (especially if you’re not local), but I’ve also read mixed opinions about whether they really perform as advertised once you factor in management fees, maintenance, and long-term expenses.For those who’ve bought turnkey rentals:Did the numbers hold up after your first year or two?

Most people judge syndications simply because they don’t understand how they work, and many jump in blind without knowing how to vet sponsors correctly or stress-test deals.

I want to make this transition as smooth as possible and avoid stepping in as the “bad guy” trying to change rules or expectations.What’s the best way to structure my offer so I can get vacant possession without causing stress for the tenant or the seller?

Coordinate with the cable company as we do a 25% partial-stress of the cables within 24-48 hours.

Quote from @Kerlous Tadres: Honestly, I’d just hire someone this winter so you don’t stress about it.

Adding the ability to run sensitivity analyses for ARV, rehab costs, or holding period can help flippers stress-test deals and make the tool valuable for regular use.