When they go in for a maintenance request, they will look around the property for me to see what condition it is in.

Based on you situation and property they may suggest one or the other type of coverage.If possible get quotes with Special form coverage and the building valued at Replacement cost. 

Looks like its cold plunge at the beach for me

I'm in Four Corners but I'm in a community that specifically allows STRs in the covenants, so no issues for me.

I've seen DOS happen a couple of times, I don't think it is all that common. 

A few things that come to mind for me:-I wouldn't put the cleaning fee as a monthly line item at $400.

I know on flips it is considered traditional income due to being classified as a dealer (someone who buys for the profit of the sale) and not an investor (someone who buys for the profit from rental or other forms of income) but what if you bought and renovated a property and held it for one or two 12-month leases?

So not a 180 but if common sentiment is this direction, then it likely won't happen that way.

got to love a government form.... 

There's always pros and cons to every form of item we use in construction.