Contact some collection agencies that operate in your market and see how they operate.

You can rent long term, but short term rentals would be hit or miss. do some homework on that market.

The shed should be entered as an asset and deducted in full via bonus depreciation.

If a room has their own bathroom, obviously that would not be part of the cleaner's responsibility as they would not be entering any of the private spaces.Renting by the room will get you more money, but will also require more work on your part as there will be personality clashes (do not get involved in those).

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Welcome to the Pittsburgh market!

In the VAST majority of good rental markets function is MUCH more important than form (aesthetics).

Tell squatter the judgement will wreck his credit (he probably has bad credit if he's doing this break and enter hold you hostage).

So it was a terrible start that I have significant responsibility for the issue.Just as abatement was finishing we entered Covid lockdown and a single contractor at a time working.  

Although rents were below market, it was a stabilized asset, fully marketed for sale.