We started with just a John Deere 6320, high capacity bucket, bale spear, and pallet forks.
We borrowed any attachments/implements from local farmers and have since added a square baler, brush hog, rototiller, drag, box grader, post hole digger and probably a few other things I don’t see us use often.
We still borrow/trade work for cutting hay, raking hay, and round baling. We are fortunate that we prefer to cut hay earlier than most people in this area or no one would have one to spare.
We have also since added a Ranger (similar to a mule) which has been very handy for pulling hay wagons, using the winch, moving small amounts of hay, feed, checking fences, keeping kids out of the way (“sit in the ranger while I do this thing”), etc.
Our most recent acquisition is a commercial grade zero turn. It’s great for mowing my grass trails, grass riding field and the lawn. We quickly gave up mowing the pasture with it, and hired someone with a flail mower to mow them with his tractor instead. The goal for us is a batwing mower but that’s a ways down the line, also perhaps a bobcat/smaller tracked tractor that won’t be so hard on nice grass.
I would highly recommend as other posters have suggested to make a list of the things you know you’ll need to do and then try to imagine the things you might need to do.
I never dreamed that every spring we’d be moving/clearing buckets of mud out of our “dry lots.” Buying the tractor was a huge leap and I don’t regret it at all. Couldn’t imagine doing it without it.