I'd get something like a Ford 3000/3600 or better 4000/4600 either with a diff lock. Maybe a Massey 165 or Deere 2150 or 2155. There are a slew of Deere models that would fit the bill. 5-6 foot bush hog. 6-7 foot disk. Spreader and a box blade. Probably get into all that for $5-8k.

Those would all be good first tractors, reliable, easy to work on and would do anything you need done.

A step up from that maybe a Ford New Holland 3930, Deere 2030/2440 which are stout little machines.

All 4wd is going to do is allow you to get stuck a LOT worse or rut your fields all up... OR tear your roads all up.

I like 4wd on a tractor with a loader. Doing loader work. Other than that my opinion is it is not necessary.