I like working on my own stuff - otherwise owning over a hundred diesel trucks and old tractors would make little sense. In regard to cost? I've gotten many diesel trucks for free - or next to nothing. You mention $1000? The most I ever paid - in my life - for a truck was $3300 for my 94 Ford F250 ex-cab 4WD with a turbo 7.3 diesel. It's kind of a fuel hog, but I love the truck. It came from down south - it's rust-free. It's been more trouble free than many new trucks I'm acquainted with. I just bought a 91 Suburban 1/2 ton 4WD with 6.2 diesel with a sealed-bid from a local school. Well maintained, runs perfect - paid $225 for it. Also bought three diesel K5 Blazers recently - one in very good shape and low mileage, and two others with bad transmissions - and traded 50 bales of hay for them in total - i.e. $75 for all three. About your mention of contstant tinkering? I like working on equipment when the work is planned - and not a result of breakdowns on the road. Any truck I drive on the road gets completely gone over first - usually as a winter project. In the past 30 years - I've had ONE vehicle towed due to a breakdown - that's probably a better average than many get with newer vehicles. My neighbor has a new Ford diesel and it's spends a lot of time at the dealership with problems. I also see as a benefit with older stuff - that I can easily fix just about anything without needing complex newer diagnostic equipment and/or overprice parts. In regard to only being able to drive one at at time? My wife and I always have at least five vehicles registered for on-the-road driving - and many others off-road as farm vehicles. But, we switch back-and-forth. Also have certain vehicles dedicated only for winter driving since salt ruins them. I find it useful to have a few lightweight vehicles that get good fuel mileage, a heavy diesel truck for towing, a diesel dump truck when I need it, etc. And insurance is $150 per vehicle every six months - i.e. $1500 per year total insurance cost for all of them. I suspect many people pay more than that for one new vehicle. And, in New York - inspection is much cheaper for older vehicles and cheaper yet for old diesels. I'm not claiming my way is better or worse than anyone's elses - but it's certainly better for my wife and I. We enjoy having zero debt, low insurance costs, and the flexibility of being able to do many things for ourselves - by owning many old - but useful cars and trucks.
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