John,
I'm starting to appreciate the improvements recently made in the Craftsman line. Especially, the DLT2000. It's a little bit more than $2000 dollars, but it comes with a decent Kohler power plant, Cast Iron front axles and a 10 gauge steel deck.
Understand that it is on sale through 4/20.
It might be worth the look?
Also, as mentioned by others an older JD could be easily had within your price range. I recently spotted a JD316 with 50in deck, hydro and an 18HP ONAN engine. It only had a little over 400 hours on it, and it was going for $2200 at a dealer.
I snoozed and loosed on that one.
The older 300 series are legendary for their reliability. Steer clear of the JD317. There were some issues with that powerplant , but I've heard that a number of them have a replacement engine that's fine. Someone more in the know should be able to come up with the model number to look for.
If you don't mind rowing your own gears, a mid-eighties JD212 might be a consideration. Their turning radius is a bit long, but I've seen them for around $1100-$1400 in good condition.
Scope out the local dealers, folks are trading right now and the USED market should be pretty active. Also scope out the local papers for auctions in your area. A few years back, we picked up an old JD110 for around $550. I was anything but kind to it on my rough property. But it never failed to impress. I recently sold it to someone at work who is into tractor restoration and could easily fix the tranny that was locked in 3rd gear.