I made do with a very small compact tractor, a 13hp Ford 1100. I could drive it up into the rear of my 1/2 ton chevy p/u and go anywhere I needed to. I wanted a larger tractor, and got a great deal on a JD2555. It weighs 7000 pounds and is a little much for transporting back and forth to anywhere with a 1/2 ton p/u. I now miss those quick little jobs that paid the repair/maintance bills and kept spending money in my pocket.
The 2555 will work circles around the Ford 1100, but at a price. Anything ever tears up, you better hold onto your wallet cause it is fixing to take a beating. (not that the little one was much cheaper, just different if that makes sense)
Weigh what you have to work with, such as a tow vehicle to take it to the shop, when needed, any implements currently owned or being considered for ownership. (My JD2555 made junk out of several of my lighter made implements that serviced me for many trouble free years with the Ford)
Horsepower in a tractor is great till you start tearing up things. (and you will!)
Good luck, and welcome to the board. Hope to see you sometime on my travels to Gulf Breeze.
David from jax