Should I buy a 1999 Boxter?

[qstoria]

I am going to say yes. As in yes you should buy a '99 Boxster.

Exactly which '99 Boxster though..? That is harder to answer but the one you describe sounds good on paper.

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[78F350]

Yes. For a 20+ year old car, I think that a 1999 986 is a great buy. That said, each car will have it's own history and potential issues.
If you don't plan to renovate the car yourself, buying from a reputable shop or seller who was caring and knowledgeable can make a big difference. One consideration with the Tiptronic transmission to ensure it's longevity is to make sure that it is serviced - the 'Lifetime transmission fluid' should be changed periodically, but I'm not an expert on the interval. I have seen recommendations vary from 50k miles to 100k miles. See what the shop (seller) recommends.