Until then, I'm anticipating consistent double digit increases in insurance YOY.My Thoughts:I personally think insurance expense escalators should have 5-10%(as an avg) expense escalators for the foreseeable future.Am I alone in feeling this way?

While it may pencil out on paper to do one option over the other using simple math I would urge you to think big picture as well.

I think your being in Florida may not give you the full picture here. 

BP fam what are your thoughts on my scenario -- I bought my primary home for $335k 2 years ago and have put about 40k in upgrades (new double paned windows, new foundation, new metal roof, rain gutters).

Make sure that you have a clear case for all of those repairs: before and after pictures, move-in form, etc The more evidence you have against them, the easier it will be to proof if they decide that they don't agree with your deduction. 

If they are doing a 2% and 8%, then the sponsor management fee is double the norm.

All that double entry in two software - sometimes I shiver at the thought of the overhead.

Half of my portfolio is OOS, and I haven’t seen most of those, even after 10 yrs, but I get trusted people to take pictures and I send specialized trades (plumbers always and sometimes electricians) during DD period.

But for sure have an agent that is local do a drive by snap some pictures and give you a price assessment to see where your at. 

If you want double entry accounting, flexibility, and solid support, REI will allow you to manage your rentals on your own.