(rents are increasing in the area, but we are heading into fall/winter where the tenant pool is lower) Assume that you would get pretty much all your money out on the refi.

I evacuated to Dillon years ago for Hurricane Floyd and the hotel across the street did not bring in the pool furniture. 

You probably don't want to buy in A neighborhoods because if there is a downturn you don't have a large tenant pool, if you buy in B neighborhoods you have people moving up and moving down.We only buy houses we would be comfortable living in ourself, not just the neighborhood. 

Example of issues: front window squeals when windy outside, lots of concrete around pool is severely cracked.

The concrete pool hasn’t been used in years.

Waterville Estates (in Campton and Thornton) is good for rentals because they have night skiing and a great rec center with pools etc but the property taxes are TWICE those of either town because they're a 'village district', which adds it's own taxes to the town tax - it may still work numbers-wise, but worth knowing about nonetheless.

Prevents any issues coming up later when you want to sell the property or when the county sends drones through your neighborhood looking for unpermitted pools/decks/carports, etc to try to raise revenue to cover unfunded liabilities in government spending. ;-)

I worry because quite frankly our tenant pool isn't one that adapts super well to change, they aren't that technologically inclined (online / app = payments - lol - some of these folks are depositing cash into our bank accounts on the 5th) and I worry that this change will disrupt, cause move-outs, more fees, etc...Thanks in advance for your insight, heckles and advice.

I wouldn't have a rental with a pool. 2.

You can also pool funds together do that you don't completely deplete your savings and have some working capital available for your rental property.