@Lou Ruggieri,alternative thinking:-clean basement floor to perfection-waterproof membrane/ couple layers of exterior grade paint (encapsulate any asbestos dust)-exterior grade carpet : because you are up north/cold floors; if flooded, can be taken out, disinfected and hosed out, dried out, replace backalternative thinkhing2:-clean basement floor to perfection-waterproof membrane/ couple layers of exterior grade paint (encapsulate any asbestos dust)-treated 1x1 (as "ribs"/"joists")-lay exterior grade plywood/ost on top of it-floating floor on top of that: preferred here is Allure LVP from home depot, but many available from reputable manufacturers; probably floor needs to be rated for under grade/basementsortile everything and provide rugs + non-slip underpads

Will I have to replace the damaged windows and doors?

We tried really hard not to overbuild and over buy, but we had to replace and rehab the things that needed it.How do you all let the the appraiser know all of the details of your rehab, and how far into detail do you go with them?

We slow rolled it, but now we have around 4M in property and all the though we are not rich and have not replaced our W-2 job (yet).  

I've replaced all plumbing (freeze damage) and completely renovated one of the apartments.

Expect to replace within 3-5 years. 

The owner has already looked into replacing boilers.

What about replacing the roof?

I'm contemplating taking the Directv received out of the unit and replacing it with a Roku/AppleTV/Google Chrome, etc. to offer streaming services, or maybe a DVD player with access to those streaming services. 

I've seen "permits pulled" before for only something simple and unrelated, like drywall replacement in the 2nd unit, with the owners insinuating the permit was for the addition as well.