My apologies. I just double checked the classifieds on Turfnet.
Brad Fox is located in Basking Ridge, NJ... which is a whopping 2hrs away from you. I also checked the entirety of their rotary mower listings. Out of all of them, the closest unit to you and your price range, was this one:
Jacobsen Turfcat 428D - Used For Sale - TurfNet.com
These are great units, and you could probably negotiate a bit off the price... but I'm assuming you have nearly zero interest in travelling 2hrs to buy a mower.
Sorry for the misinformation. The market was thick up there last year. It could be again this year, when the spring selling season picks up.
As for new unit in the $2-2,500 range, I can personally speak for the John Deere D140. My wife had one when we met. It had stood up to her abuse for several years, and is still in operating condition today. For the price point, it leaves an amazing finish. It's not very fast in high grass, but that shouldn't be an issue for you. As for the transaxle... it doesn't leak, and still has the same power transfer as new. If you knew my wife and the abuse this mower had been through, it would testament enough for anyone... and she was using it to maintain 3 acres, not to mention a little over 1/4mi of roadside on both sides.
The only reason we stopped using this mower and bought the Toro, is because we opened up our 3 acre yard to 5.8 acres. It took up our whole weekend to mow it with the D140.