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. 

My sacrifice… no haircuts and no fast food. 1 job full time, 1 full time side hustle. 0 debt at the time other than student loans.

Often times they come back with a list of repairs that they would like to see to protect the home or mitigate liability. 90% of the time those items were on our list to fix anyway, and sometimes we even haven't done before we get the letter from the insurance company.

I do not think they regulate this strictly on other industries like food service, or even medical.Sounds like the mayor or city planner or someone "important" had a bad stay at a STR somewhere.

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

You and your partners are going to do nothing but put food on the table for your GC, Agent & PM.

There are state specific items to take into consideration.

The best defense against rats entering your property is to seal off all entry points (holes, cracks in walls), remove food sources (dirty dishes, food left in trash cans), and water sources (like leaks). 

The itemized damage estimate that my insurance provided me lists an Actual Cash Value that is 15% higher than my Dwelling A Coverage. 

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