Also, they recently increased the HOA fees, which is definitely needed, but it didn't come without a fight by all of the in residence owners who have been living there for 20 plus years. 

Are they fighting with a spouse/partner/roommate and need a place to live ASAP?

Tenants will often fight to stay in a space they know is a great value that is hard to find elsewhere.

I wanted to ask if anyone has thoughts on fighting to have your FEMA flood insurance lowered.

No giving the buyer 3% closing assistance or fighting repair requests, financing falling through, or appraisal shortages.

Fred Heller is right in that an estate attorney needs to review deal for Widow as we don't know how things are titled, is there a trust involved, is there a will and or if there is going to be fight over Husband's estate from family or anyone else.

The time when that would come up is when a borrower wanted to fight you.

The enrolled agent on this site also goes onto state there is case law (court decisions) that were in favor of cost allocation on Sch E, but the actual cases were not cited, and that if you were "aggressive and willing to fight with the IRS" the case law might actually support this.

It just seems every time I turn around taxes are going up or I have to fight the assessed value. 

I have found getting tax values lowered tends to require a big fight, and they don't like doing it outside of their assessed year.