Although most of my stays are <7 days, I've had a few longer stays (business travelers and a family that was going through a full home remodel).

Once, somebody older from our family mentioned that the sofa bed wasn't that comfortable if you sit for a long period of time in it.

Then keep the speed of money & time moving to make more money in the end.

Needs gutters, full kitchen and bath, floors, paint with some drywall repair, windows, front porch and the deck on the rear is pretty poor as well.

@Matt Smith the reality is that Chicago is full of "non-conforming" units.

Utilities- if you're doing a full-blown subdivision you will need to run all of the utilities yourself. 

This left the remaining roommate in a difficult situation, and he is now trying to find a new roommate.I have informed both tenants that they are equally bound to the 12-month lease agreement and that rent must be paid in full, regardless of one tenant moving out.

Not worth my time and piece of mind.

.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

@Alejandro Martinez I'm a fellow Canadian from just down the QEW from you (Hamilton) and moved to Orlando just over 5 years ago to invest in real estate full-time.