Most of what I do is move round bales, mow, and drag the riding arena. Miscellaneous is anything I can think of with a grapple, plant fence posts, spray chemicals, broadcast seed and fertilizers.
I started with a small 1956 Harry Ferguson. That was our first tractor and it was okay for a first machine. Next was a 32 hp machine with MFWD and a FEL. Better tractor until we moved away from square bales and started doing round bales. Next up was 60 hp open station tractor. After a few years of mowing in 100+ weather, we moved to a 83 hp cabbed tractor. Had that for 7 years (issues with support from the dealer and manufacturer) and finally ended up with a 90 hp tractor.
This beast is about as big as want to go for the size of our farm. It is capable of doing everything we need and still small enough to fit where it needs to go. A few more horses would have been nice. Running a 15 foot batwing mower would be nice, but more power means a bigger frame. A bigger frame is a larger tractor and maneuverability suffers.
Plan out what you intend to do today and in the future. Buy accordingly. I would rather err on the side of too large than too small.