Vell Buddie, Naw your tawkin' my lankwitch! (It's very difficult to type with a PA Dutch accent!)
As an old PA farmer, let me expound on tractors. Old, serviceable, running tractors can be found on Craig's what-ever-you-call-it. You could probably move and launch any trailerable sailboat that was brought to the grounds using a regular towing vehicle like a car or pickup truck. 4 wheel drive tractor would be more expensive. A full sized Farmall, Allis Chalmers, Ford, or Massey Ferguson would do the job. Gas or diesel powered. Gas powered would be less problem if you ran it out of fuel (diesel tractors are more difficult to bleed than the reliable yanmars, universals, Perkins or others) or if you wanted to use it in cold weather. A dependable full sized pickup like a Chevy or F 150 would be nice too. If a truck, then definitely 4 X 4. Driver could remain out of the weather too.