We ended up negotiating a "cash for keys" deal which in the end was much cheaper than an eviction attorney.

Cost segregation is more of a cost estimator, contractor, or engineering exercise than an Accounting exercise.  

The school boards monitor property sales closely: in your example of a house selling for materially more than an appraisal then the schools will request a tax reassessment.When I’m doing my due diligence I always assume that a) taxes won’t go down even if I buy at a discount; b) taxes will immediately reassess in the first year to the new price, which has happened to us on most purchases.Note there was someone on a bp podcast who created software that auto-populated the forms needed to challenge the assessment.

What I would like to do is to change this to exhaust outside.  

It may be "normal" but it sounds more like a formality than an inspection.

After owning them for 5 to 7 years, we made the move to sell, and did a 1031 exchange into an 18 unit property that I found after an exhaustive search in the same town.  

If I help my landlord with simple maintenance, caulking, fixing can light fixtures, replacing an exhaust fan, can I deduct on my taxes the material costs and or labor since I performed this work for a rental property I do not own?

I checked the forums, but couldn't find an exhaustive resource for legal requirements.

After you have exhausted conventional mortgages ( or in between loan availability) you start looking for PML and owner financing for long term loans.  

That type of policy provides an additional layer of Liability coverage (usually in $1,000,000 increments) that start if the primary policy's Liability limit for the location gets exhausted by a claim.