i was in the exact same boat back in the fall..........
weigh your options......the money you would give to someone to come and do it would be a GREAT down payment on a tractor or the implements.......i'm not much for buying new but there are some great deals out there right now.....
to get started, don't rule out those older fords, massey, etc......you can buy a pretty nice older tractor that has the hp you are looking for, for the amount you have to spend.........of course there is always bigger and better but that can be bought later- especially if you are hesitant to spend money right now, with the economy and all.......
AND, think about this, i was all gun hoe to get out there and get that place cleaned up so i could see what it looks like.........i got it all cut back, but now i'll have to keep up with it.....the weeds, briars, whatever that crap was, had just about everything choked out.........other than trees poking through, i don't think another 3 years would have really made any difference in how it looked or how bad it was.........remember, it has been growing up for a long time, another 3-4 years probably won't matter much.......
my wife's uncle called last night and said he found a ford 5000 (think it was a 5000??) with a loader for $5000 and another guy had a nice one with no loader for 3500.....
as much as i love the ole' 8N fords, love the ole' flathead v8's, etc, they just won't handle what you are wanting to do....yes, you could baby it and be very careful, but i see lot's of holes in your radiator, holes in your tires, lots of tinkering (if you don't spend a lot of time touching it).......now once it's all cut back, then the 8n, with lot's of seat time, would keep up with it
shop craigslist.org and on ebay for tractors that don't sell...don't meet the reserve, etc. then call them and make an offer.....a lot of people seem to be unloading their older tractors and buying these new 4x4 diesels, so there are deals to be had.....