Sean,The rental dwelling market for many areas in the Northeast have seen both rate increase and Insurance companies pulling out.  

Have seen some great flip/BRRRR opportunities for cheap in Chattanooga, TN.

High property taxes might be offset by better rental rates, or vice versa.

If due on the 1st, do you pro-rate the tenant's portion of the rent for the remainder of the month when the lease starts and also prorate their portion for the days in the last month up until the lease expires?

It's extraordinarily cheap.

There is a high percentage chance that those closing costs are actually going to buy down their interest rate.

Alternatively, should I wait for better rates before making any moves?

Surveys are my area of expertise ;)Ultimately, I tend to agree with you that allowing pets, with specific guidelines and screening criteria for good pet owners, will often yield greater occupancy thus allowing you to increase rates.

By the time they finish building it anyways the property values will have likely doubled at the rate we are going down here... and a new vacation home is never a bad thing lol

You woul get signiture loans from banks for half the rate from that credit card.