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Thanks for all the feedback/ advice. There's a number of relatively simple/ cheap repairs that *could* fix the problem, but worst case its a complete overhaul, so its really a bit of a gamble. I guess what it really comes down to is if these tractors were designed/ built to be overhauled or...

Is your 5k estimate for having someone do the repairs or a DIY overhaul? It's got about 1900 hours Yeah I'm really on the fence, it's an opportunity to get a more capable tractor than my modest budget allows, but also don't want to get into a gigantic money pit project.

Im going to look at an early 90s L Series which the seller says has blowby and thinks it needs a ring job. Apparently it is bad enough that it doesn't like to start with just the starter motor so they drag it with a truck and bump start it to get going. He said it runs fine but smokes a bit...