IMO - these are the things we considered a few years ago
Low hour used will save you some money. Depending on the use, you will probably put only 100 hours or less a year on it going forward.
50 HP is a decent sized utility tractor and can do most of daily chores. Assuming you need a shredder, what size to do you want and can it pull it? Other implements?
Can/will you trailer it yourself for any major repairs?
What dealership is closest to you - Deere or Kubota.
4WD is almost a given and I rarely use it, but nice to have when I get in crap
HST transmission - easy to use and wife/kids/parents/etc can all drive it without too many issues.
Cab would be nice for the summer etc, but we do not use it enough and we could not store in under the shed.
FJB, FPA, and FAZ