My 2001 Boxster base is manual. I have never tried tiptronic except in a 911. I do like shifting gears as it is my preference. You should try both kinds of trans. I find living in a large city that I end up using gears 1-3 to keep the revs up. Tiptronic is good if you want to be hands free in a busy stop/go traffic. If you think resale it might be harder to sell a tiptronic.

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