As you can imagine, a few tenants have work schedules that make coordinating entry difficult, and there are also one or two who tend to avoid cooperating.Since the township sets the date and time.

Professional-level reporting that’s easy to export for accounting and tax prepOther platforms we’ve tried:Hemlane – A solid choice for landlords who want to stay hands-on but need help coordinating leasing and repairs.Doorloop – Clean interface and easy to use, but we ultimately switched back to Buildium for the deeper integration capabilities and more robust accounting tools. 

Add a smart lock (like Schlage Encode or August) and you can manage guest access codes remotely without having to coordinate key drops.If you already paid off the ADT equipment, maybe ride it out until your contract ends — but if you’re on a month-to-month, switching will save you money and give you more control.

I use buildium, it is on the cheaper side of the online platforms that help you coordinate all stuff within one place from request for maintenance and other stuff like emails to tenants.  

You can sell multiple properties and roll all the proceeds into one or two replacements without triggering tax, it’s called a “multiple relinquished property” exchange.The complexity mainly comes in timing and coordination.

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?

Coordinating the sale with other income events, like delaying bonuses or capital gains, can help keep you in a lower bracket.

I mainly focus on the Midwest, and what I’ve seen work well is lining up a property manager who can handle both mid-term and short-term rentals, coordinate cleaning, and market the unit effectively across platforms.

Keep your bill-paying job for stability and build paid reps inside real estate: target three roles you can do part time now 1) assistant to an investor-friendly agent pulling comps, writing summaries, and hosting showings; 2) acquisitions runner for a small multifamily buyer doing photos, repair bids, and rent surveys; 3) leasing or maintenance coordinator for a local property manager to learn operations.

Well I guess because it does require real work they have to actually find the deals coordinate the rehab and get them sold..