My advice is to buy the biggest tractor you think you will need the first time. It is easier to do little jobs with a bigger tractor than it is to do larger jobs with a smaller tractor.
Another question, How happy is a FEL on a farm tractor digging into natural gravel banks? I need a few dozen yards of material to raise my driveway in spots. Can a 65 hp 4wd tractor fold up a loader easily or does it take some real effort? Right now my "equipment" is a 300 Kingquad which seems to be totally idiot proof, in terms of plowing and towing.
I am adding up all the jobs that need to be done now or soon to sell a tractor to my dear wife, its getting pretty close to the price of some of the tractors I'm interested in.
Just keep in mind that you need $ left over to buy impliments.
you could have the biggest tractor you'll ever need but if you have no money left over to buy a box blade or bail spear or pallet forks or brush hog then the tractor is fairly worthless on its own.
If you can fit in those areas that the little jobs are located.
Kind of like buying a used car. Check under the hood and kick the tires!