That's a pretty big chunk of stuff to do and you'll probably have a million questions about things you discover while studying these things.Good Luck!

Forget about it" The nursing home stuff is pretty gross.

We went back and forth with them trying to get stuff out they wanted.

Now if I remodel the kitchen, bathrooms, doors, windows and some other stuff I could probably rent it out for $650-$700, increasing my cash flow, specially when I move out.

I like the idea of short/mid term rentals more then the long term...one big reason is not having to move all of his stuff...or at least being able to take my time.

If the new tenants want to move stuff in early, they need to pay rent and you need to talk to the old tenants. 

If you can find a 4 family in MA with centralized heat (oil or gas) and knob and tube wiring you could get $60,000 from mass save for your project plus a bunch of free stuff.

Emphasize that if they are experiencing illness, its your priority to make sure their health is not affected and the only way you can do that is if they vacate the unit so you can properly and thoroughly mitigate the issueThis is  shakedown.....Damage to their shoes etc.... that's what renters insurance is for... not your problem.Mold remediation....90% of that stuff is a frickin scam.

They also had a bunch of stuff in the side yard. 

The management LLC does literally all management activities-- hire PMs, hires contractors for renovations, hires the legal experts for other stuff, buys STR furniture, hires interior designers for STRs, hires pest control, etc.