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'83 Mercedes diesel 300k+ still going and I will keep it going indefinitely. It just makes sense as a car for me. It is comfortable and reliable. I know it well. It gets great mileage, will burn anything liquid, and can actually haul a lot more that any sane person would put in/on it. (I may not fit into the sane category) Even if I come into infinite money somehow, I would still keep it... likely modify it a lot, but still keep it.
'84 F250 diesel... similar to above but bigger and a little worse mileage but it is my offroad and hauling pig. Currently a huge work in progress but when finished it will be able to take me just about anywhere connected by land, sustain me nearly indefinitely, and will be able to haul all the junk I could ever want to at the same time. It too will be kept basically no matter what.
I also have a few motorcycles. These I can actually see getting rid of a few.. tailoring these to my riding style.
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boom
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