This property has 4 bedrooms and only 1.5 bath, which I worry is not ideal for this type of living situation.The house is a split ranch with one car garage and 2 car driveway.

I may drive up and live out of my car for a few days.

If there are utility bills, car payments, that sort of day-to-day necessity items, that's not good.2. 

Quote from @Carly Lanter: Hello all, Newbie here! 

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?

Most of the returns come later when the deal sells, not month-to-month like a direct rental.Also, keep in mind that with syndications you’re not the only decision-maker.

I am renting to a Car Dealership, and no insurance company seems to want to give me Landlord Insurance for the property.

No heavy rehabs.Use private money or short-term capital to acquire them.Structure that private money to be paid off within about 5 years - smaller loan, faster payback.Then sell the property on terms using seller financing with a 30-year note to a family who wants to own, not rent.The buyer makes fixed monthly payments for 30 years.After the private money is paid off in year five, the income continues for another 25 years - steady, predictable, and debt-free.In simple terms:You’re financing like a car loan but selling like a mortgage.The result is a portfolio of free-and-clear homes that still send monthly payments for decades, without renters, maintenance calls, or refinance risk.Why it works:Shorter debt horizon = faster path to financial freedom.Selling as-is means no rehab costs or turnovers.Owner-occupants take care of the property.Payments are consistent and long-term.It’s not about leverage.

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One single car garage (240 sq ft) for $17,000 in three months.