@Bobby Shell doesn’t sound like something you’d want to put a claim into insurance for.

No, the rental mortgage principal is not an expense so can't be claimed.

The reason being that we make too much from our W2 jobs to claim depreciation.

FSBO sellers are notoriously overpriced, under-repaired, and unrealistic.

In Maryland the tenant can stall the process by claiming an escrow complaint. 

@TJ VerdiglioneJust remember you can only claim what is owed on the note.

Homeowners insurance claim for new roof/gutters and exterior paint.

I was told that my only option for removing them from section 8 program was to actually start eviction or small claims suit.

As far as insurance goes, there's no secret that a claims department's role is to figure out how not to pay your claim. 

In addition, you'll want to be sure of what restrictions and easements will survive the sale and you would take title subject to.I'm not an attorney and this is not intended to be legal advice, it's my opinion based on my years of handling title insurance claims across the country for various underwriters.