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?

Here's the deal:4% I/O, 6-year balloon25% down, $650K owner-occupied homeBorrower is primeI guarantee first $75K of lossesEffective LTV ~80% after guaranteeWithout the guarantee, I'd expect maybe 85-90% pricing based on what you said.With the $75K guarantee bringing effective LTV to 80%, could I get closer to 95-98%?

They all should have projections over the life of the DST and show where the jump from I/O to amortizing happens and how much it is.

@Curt Smith I do have the app.

What apps or tools do you use to manage your flip projects?

. - I find it amusing that they show a graphic of an app showing investor returns over a 10 year period when they haven't been in business half that time. - They show a little map saying they have analyzed over 20 markets across 11 states. 

btw, my tenants like the app as well.Good luck! 

The biggest fixes are using a dedicated bank account/card per property (or at least per portfolio/state), doing a monthly close (about 60–90 minutes) to categorize transactions and flag odd items, batching receipt capture weekly or monthly with a single habit (photo → app/email), and using tools like QuickBooks or Stessa with bank feeds, rules, and receipt attachments so you can generate a clean P&L by property and instantly answer questions like “how much plumbing in FL,” which removes the scavenger-hunt stress and makes scaling to property #11 manageable.

The last loan app I received was from someone who had purchased something like 14 facilities in the last 18 months.  

Especially since they started allowing people to apply through a browser and not forcing them to download the app.