I looked at the Massey 35 last week and...

...the tractor looked like it was in pretty good repair. I don't know alot about tractors to start with so I approached it like I would an auto purchase. He says it is a 1958, he bought it from a guy at an auction about 3 months ago. He doesn't use the tractors but he likes to have something to trade with. It is the 4 cylinder/40HP. The only thing that troubled me was the engine had black stuff around it and everthing else was pretty clean. Don't know if this is oil leaking or just regular wear and tear. Any thought? He has an old brush-hog to go with it - pretty rusted on top. Some things have been replaced like belts and exhaust pipe, tires good. He's asking $3,200. When I asked him how it runs he said he hasn't run it but he and his grandson drove it around some and it was fine..."but that you don't know about these old tractors, they might run 3 years or one day..."
OK. Now if this was a car, i'd have a better basis for making the decision based on what I'm going to use it for. I'm looking to use this everyweekend or so during the warm months to dig post holes, aerate land,plant/cut alfalfa hay and grass and grade my driveway.

What do you guys think - is this the kind of tractor I should be looking for? Any and all feedback will be much needed and appreciated! - Will

Make sure the hydraulics goes up and down okay. It's normal for them to drift down after the engine is shut down.

See if the brakes work.

If it all checks out, and it doesn't have to be perfect, but all that stuff should work within reason, then the price seems okay. Especially so if it's Canadian. But a 35 in usable shape would probably bring about that most places in the US as well.

If the machine is sound it should do the kind of things you describe.