If someone gives me a way out or a reason to get out, I get out and never look back.Do you know other investors in real-life? 

A business/way of life to continue? 

If you do 203k loan (FHA renovation loan), you can wrap the reno into the loan, but it is a bit complicated on the back end with the draws to the contactor.You are using a lot of book words that may not go together in real life so you want to start going to meetups in Des Moines and meeting other investors so you can see what they have done.

I don't want to be frugal as to not enjoy life, but also not enjoy too much where I have nothing to show for the future. 

By default depreciation is straight line taking a flat amount per year based on the expected life of what you are depreciating.

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

There's no better person to follow right now.Check out Set for Life by Scott Trench.

My entire life pops up on google.

Other option is giving a small portion of equity and splitting profits and ongoing costs evenly, but not sure how much equity to give or how to logistically buy their equity out later on if I want to keep the STR for life.

Since in Florida there's only one major insurance which is run by the state it's called Citizens they require an inspection in order to determine if they will insure you or not.And yes if the inspector gives your roof no life left this they will not insure you.