Woods makes a very good bushhog - I've gone thru several different brands in the last 20 years, and the Woods has served me best. Get one wide enough to cut out your rear tire tracks - probably a 6' will do nicely for the size tractor that's been recommended.

A sprayer (3-pt hitch type for the tractor) might be another addition to the equipment later on - great for keeping noxious weeds in check and doing some spot spraying along fence lines and covered areas. Works well on the multiflora roses, if you have those there.

The advice to pick equipment from a local dealer with a service department is worth following, and I'm speaking from experience of NOT having done that on occasion! Lots of good information from folks on this forum who know their subject (not that I'm one)......