Forget the Sears and the JD GT245...

Simplicity Conquest or above

John Deere X5xx or X7xx class

Smart move would be to look for a clean used sub-cut tractor like a Kubota BX.

Thanks for the info! The tractors that I listed above are the only used garden tractors that I found within my price range (up to $3000) on eBay. I would love to be able to get a Kubota, but the price is beyond reach for me; the LD X5s 7 X7s seem to be just beyond me too. I have visited a few local dealerships to look at their used gear too, but their prices were darn close to what you might pay for new...
The catch-22 is that I am paying someone else to mow while I am without, so that makes saving a little bit harder. I was hoping that there was a 'magic bullet' that I hadn't found yet that would address my needs!
Thanks again!

The best deal around is a dollar's worth for a dollar. Many people want to pay 75 cents and get a dollar's worth but almost always they end up spending 75 cents and getting 50 cents worth.

No one gives working tractors away for nothing... you need a real garden tractor and actually that would be small based on your post.

Sounds to me like you have a LOT of work for a heavier-duty tractor. Have you considered some of the really amazing financing deals there are out there lately?

The true cost of your tractor, is not the purchase price, but rather, the depreciation between the "purchase price vs resale value". With so many 0% financing deals, or very low interest leasing options currently available, you might find that you can get the "right" tractor for your needs, then sell it off for very little loss, once the bulk of your heavier work is done. You could then buy a smaller tractor for routine yard maintenance (mowing, snow-blowing, etc.

My local Kubota dealer offered me some amaaaaazing deals. Long-term 0% financing, or long-term leasing options, at 2.49%. With the lease, they could structure the payments to whatever suits me. Example, lease for 4 years, at 2.49%, and at the end of the lease, I pay $1. and the tractor is mine, or,,,,, if I want lower monthly payments,,, they simply restructure the payments to a lower amount, with a larger buy-back at the end of the lease.

Let's say I buy a $15,000. tractor, and use it for two seasons; if I can re-sell that tractor for $12,000. in two years (still under warranty, btw), then my "real cost" is only $3000. to get all that work done. Might be worth considering. Finding the right kind of dealer, is the key to working this out.

With that much land, consider a used compact tractor like this Kubota with 60-in. belly mower for just a little more @ $3500, since you're looking on ebay. That price may go up a little before the end of the bid but there is another one like it @ $3200 that needs a little head work. It will handle all that grass (already equipped with turf tires) and drag trees all day long, on a diet of diesel. Plus, it's got a hydrostatic tranny. Now that's a lot for your money.

Here is a link that might be useful: Used Kubota w/ belly mower

Oh man,,,,, why can't I find deals like that one, up here in Quebec. Heck, I'd drive to Florida, to pick that one up. WoW!!