I have the same issue. We bought 6 acres of land surrounding our current property. It's fairly rocky in some of the lower spots (grapefruit sized rocks or larger), and I've hauled out many buckets full. Anyway, I didn't do anything with it right away and weeds took over, so I just ended up mowing it. It's so bad that I swear I'm 2 inches shorter when I'm done with it.
I talked with a local farmer and we kicked around a plan of him plowing and disking it, and planting it in alfalfa. In exchange, I let him take the alfalfa for however many years it takes to pay off the seed and his work.
The good part is, I wouldn't have to mow the land (except for a small camp site we plan to make), and I wouldn't have to pay for seed and working the land. The bad part is, he said a ballpark estimate for him to get his money back would be 5 years...which means I couldn't do anything else with the land until he's done with it (or pay him off before the end of the 5 years).
I'm thinking of doing it myself now that I read this. Maybe I could find a used disc harrow and chain harrow somewhere. Seed is expensive but I already have a broadcast seeder just sitting here (used once and paid 100 for it, couldn't pass it up even if I wasn't going to use it right away). My only fear is not being able to water that much land, and wasting a lot of $$ in seed if things don't pan out. My wife knows somebody who will give us 2 or 3 baby miniature horses and I think that would be cool (plus I would get to build them a little barn). I don't know, I don't mind the work but I'm undecided yet.
What would you do...have the farmer do it or try to do it yourself?