I know they won’t allow double paned windows.

I've called several insurance companies and no one wants to insure it due to the old style panel. I

@Alyssa DyerSimplified numbers are 255k offerPITI $1400Other expenses include repairs, cap ex, insurance, and PMI $400 Rent front 3b2b $1300-14001b1b in law (once I move out) $700-800New roof and all new double pane windows.

With everything else that you've mentioned he has going on that is just one more emotional strain (letting go of it).

I ordered some double pane glass for the front door and back transom. 

Also, I once had this issue where tenants subletted to new occupants before I bought a property and they wanted their security deposits back, which was a strain/problem to deal with. 

-The back bedroom window in unit #2 has a broken seal and moisture staining between the panes - recommend having a window professional repair.

Seems like you have a good relationship with her, but adding a financial aspect to a family relationship can definitely put a strain on things even in the best case scenario.I'm probably reading way too much into this (again, sorry!)

COVID has changed everything and created tremendous stresses on a housing situation that was already strained.  

What is more, there is no inspection sticker on the breaker panel. Is