If you're looking for a well-built older machine, consider a JD 445 garden tractor with a 48", 54", or 60" mower. You can get them for between $2,000.00 and $5,000.00 depending on age and condition. They have a 22 hp 2-cylinder water cooled engine and hydro transmission. They usually last between 3,000 and 4,000 hours.
The transmission is rated to pull at least 2,000 lbs. The fluid can be easily changed, and it uses a spin on filter.
I have an AWS version built in 2000. It only has a little over 650 hours on it and is barely broken in.