"Chores would be pulling around empty wagons, a tedder and rake".
I would look at what speed selection each tractor has and how well they are suited to your needs for haying. I think an H has 5 gears with 4th being around 5 MPH wide open and 5th being 16 MPH road gear. An H with a 9 speed conversion kit would have 4 extra gears between the standard 4th and 5th gears. A WD has 4 gears? Oliver 77 and late Deere A & B all have 6 speeds and are better suited to haying, unless you want a slow tractor for young kids to learn to drive on.
A slightly newer tractor might have faster gears better suited to your needs and better features and still be in the $1000 to $2000 price range: live hydraulics, live PTO, better ergonomics, stronger hydraulics, etc. I would look at IH super H, 300, 350, Oliver 66, 77 (6 speeds), Deere 50, 60 (6 speeds).
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