I'd prefer a gas over diesel in the winter. However a lot depends upon your mechanic skills and what you can work on. Diesel injectors and injection pumps usually need to be taken some where to get fixed and read all the posts about gelled up diesel and having to drain and bleed off everything. Points, plugs, wires, dist. cap, etc. with a gas can be an easy tune up.
Don't overlook something new at the dealers. John Deere and the others offer financing packages to part time farmers with their country estates and then you end up avoiding a lot of problems with old tractors and something your wife and kids can start and run easy. Can be about like buying a car.
You never know when the old tractor may need a new hydraulic pump or overhaul or need some hard to find parts. Plenty of guys here are DIY mechanics who aren't bothered by that but sometimes those old tractors can be a Fix or Repair Daily that nickel and dime's you to death.
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Today's Featured Article - Product Review: Black Tire Paint - by Staff. I have been fortunate in that two of my tractors have had rear tires that were in great shape when I bought the tractor. My model "H" even had the old style fronts with plenty of tread. My "L" fronts were mismatched Sears Guardsman snow tires, which I promptly tossed. Well, although these tires were in good shape as far as tread was concerned, they looked real sad. All were flat, but new tubes fixed that. In addition to years and years of scuffing and fading, they had paint splattered on
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