I was in a similar situation and never regretted getting an older (900 hours) Kubota G1900. Diesel, 4-wheel steering, 60" deck, power to spare and moves faster than I need. As a matter of fact, I picked up a second one and just sold it recently for $1,225. It was older and had seen a bit more wear, but it ran like a top and I'm sure the new owner will get years of service from it. Watch CL and you can pick up a nice G1900 or G1800 (same mower except 1900 has one more HP) for $2k or so. I basically paid what I would have for a higher end box store model and bought a used really nice machine that will outlast any big box store model.
Good luck.