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Sounds weird, talking about a guy "doing the math", when it sounds like he's "trading in" and buying new. I could be wrong about that, but that's how it sounded the way you worded it.
When I "did the math" a while ago, I discovered buying new vehicles sucks, and trading in my old car at the dealership makes it suck even worse. Granted, not everyone has time to wrench on their own cars, but doing my own maintenance when possible is a gain, and if I can't do it on my own, working with TDIClub members to get the work done is a huge advantage over the dealership.
Another big advantage of buying used is knowing what to avoid. An example being the auto tranny on the MkIV generation of the VW Jettas. Not that I would've bought a slushbox anyway, but for those that want / need an auto tranny, it's preferable to learn from other's experiences than discover major issues on your own.
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