WC is great - great schools, lower taxes.  

The third building is on its own piece of land with a separate tax ID.

Before going into this, though I would be very conservative in your analysis of cost to renovate and what you think market rent (along with increases in taxes and insurance) would be so that once you are ready to refi into a longer term loan, your DSCR is rock solid and so is your cash. 

Tax.  

Any other surprises such as higher tax rates, preservation requirements, flood insurance, etc?

If they are going to cover business activity, you can bet your bottom dollar that the insurer will review all of your practices and procedures in order to determine whether you are doing things safely and in a law-abiding manner (see above, first paragraph).So yes, get plenty of insurance, and a corporate entity between you and your adoring public may be most convenient (consult your lawyer as to whether and what type).

The seller needs moving money, there are oftentimes an arrears that has to be paid on the loan, there are oftentimes HOA fees that are due, there are title costs, there are escrow costs, usually there is deferred maintenance, you have to make mortgage payments out of pocket until you get a renter in there, you have to pay utilities and taxes, and you need reserves in case it all doesn't go as planned.3.

Very high probability that sometime in the future you will need to put those fees towards the lawyer fees / collections - unplanned turnover, etc., 

Since land values tend to be higher in the resort areas, that can have a negative effect on tax benefits.

Vacasa Guestworks(partial MGMNT model) says their fee of 12% is almost covered by the fact that THEY will pay the Airbnb host fee   Also they will handle the tedious filing of monthly taxes as required by my city/state regulations  I’m not scared at all to handle the online listing and am not keen to pay their 10-12% fee.