I'm pretty firm in the old junk category. I don't like the payments/high insurance/taxes that go with owning a newer vehicle and I like working on my truck. I overland a 1990 Chevy, and it has never left me on the side of the road. Its loud, theres no AC (yet), but its comfortable and goes where I need it to go. It gets me home at 75mph on the highway getting better fuel economy than the equivalent Tacoma. Yes, I've spent a lot of time working on it but that's because I like the work. I could pay a shop to do everything on it and still come out cheaper than a new truck. It's not pretty but I'm not in it for the 'gram.
The trick with maintenance items is to see them before they become real problems. Waiting until you have $2500 worth of unrelated repairs to make is not the way to maintain any vehicle, especially one that is used for towing, long distance travel, or offroad.
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