Usually if it’s a revaluation where the whole town goes up in value you see the tax rate decrease and taxes stay the same or go up a little like yours did.

It really depends on the investor, their comfort level and goals. 

Florida should be busy currently with people staying in the Winter to get away from the cold & snow. 

I stay in the basement, I went thru ups & downs like everyone else,  What has worked for me lately is renting to senior men (55+). 

I would stay away at all costs. 

Quote from @Grant Woodward: Do you get pictures from your cleaners after every stay? 

You'll be tagging transactions throughout the year with categories that fit the Schedule E so when tax time comes (if you stay on top of it) every deposit and expenditure will already be categorized and it's quick to create the Schedule E and/or run P&L reports any time you need to.

In theory if I stay "retired" from W2, for CY25, my spouse will likely work half the year and call it. 

Indeed, to stay in compliance with fair housing, you need to treat each tenant the same, so that's something to keep in mind. 

Hence, your goal should be staying on the first page as long as possible instead of picking up a few bookings from different places.