If a storm happens immediately after you replace the roof, the actual cash value is the same as replacement cost, so you've lost nothing.The only thing you would have to worry about are items you did not intend to repair

A large ticket item could eat up the cash flow for years out.  

I am adding about 20 more this year, but there's one small pocket I'm struggling with the financing on (honestly, due to Huntington Bank dragging their feet on items, etc.), so I'm seeing what other options there may be. 

This will give you one critical piece of information, that it may take X days to get an offer and sell, and the second item will give you what your competition is right now.

Then at the court you will be the "prosecutor" and must out line the violations according to the lease, and show the efforts you gave your tenant to solve those items.3.  

There are a lot of options out there.Some of the most useful items BiggerPockets members have identified are features that save time so they can spend time working on their next property.

RM is plenty robust to handle the items you mentioned.  

The PM should provide itemized items of what was done.

Here's a https://www.irs.gov/businesses/cost-segregation-audit-technique-guide-chapter-4-principal-elements-of-a-quality-cost-segregation-study-and-report to the IRS website noting specific items that are included in the cost segregation study report. hmm, that website is a 404 error.  

I am also doing a live in full renovation for a long term rental where I am project managing mechanical items and doing a lot of the interior renovations myself.