My old hunting right is a 1999 Honda, 300, 2WD, automatic manual shift (no clutch but shift with foot) and I have never thought about trading up. The 300 Fourtrax is arguably the best ATV Honda ever made in the utility line. Although it doesn't have all the bells and whistles of the new ATV's and doesn't ride or steer as smoothly as the ones with independent suspensions and power steering, but it has never failed to do what I needed it to do. I just see all the ES type stuff on the newer ATV's as something else that can go wrong with time.
As for your situation. Personally I would invest in a nice pull trailer designed for ATV use before I would drop the change on a UTV type off road vehicle. I don't know what type of hills you have on your farm, how wide or congested they are with timber, but if you could make use of a utility trailer, that would be my choice. UTV vehicles are nice, but I just can't see putting that much money into something when I have a reliable, capable ATV right now. As for the gators or mules, I've never had any dealings with them. Only Rhinos and T-Rex UTV's.
Is your ATV a 300 Fourtrax? If so, do you want to sell it if you are dead set on trading?