I have not billed out splitting a tractor lately but when you split it to fix the oil leak you are going to likely do clutches and some other things and spend some substantial money. If it is something that will bother you and you will fix someday I suggest putting as much money forward now and buying something that you do not worry about because you seldom get back what you put into a tractor in repairs. My old Ford I let a lot of things go and as long as it functions do not get too concerned with them and enjoy running it dearly. As long as you are the type of person who can shrug it off and not get concerned with it I would say you are ok. If you start fixing things like a small oil leak (assuming you are not mechanically inclined and have someone else do it) I would guess you will spend thousands by the time you were done. You might ask your local dealer what it would cost to replace the rear seal on the engine (and / or the clutch) to give you an idea what "worst case" scenario is on that particular problem.
Owning an old tractor (and using it on a regular or semi-regular basis) is a unique experience. There are people who a lot of time and effort into making them as good as they were new but they do it out of a labor of love and they do it themselves (generally). You will have to accept that some of that uniqueness is problematic such as oil leaks. If it is your intent to have a tractor that does not leak oil at all you are going to have to greatly expand your budget and I suggest you do it now rather than intending to fix this one up later. My old Ford gets repairs when it needs done. King pins and bushings are on the list for this winter as I can see air when the wheel wiggles in the housing at this point. Unacceptable on a new tractor, liveable for my old cheap tractor.
Owning an old tractor (and using it on a regular or semi-regular basis) is a unique experience. There are people who a lot of time and effort into making them as good as they were new but they do it out of a labor of love and they do it themselves (generally). You will have to accept that some of that uniqueness is problematic such as oil leaks. If it is your intent to have a tractor that does not leak oil at all you are going to have to greatly expand your budget and I suggest you do it now rather than intending to fix this one up later. My old Ford gets repairs when it needs done. King pins and bushings are on the list for this winter as I can see air when the wheel wiggles in the housing at this point. Unacceptable on a new tractor, liveable for my old cheap tractor.