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^ x2.
Late to the party here but I was in the same situation a few months ago with a budget of 40k USD to get into a Porsche again. Back seats required since I have two kids under 5. Been planning a return to Porsche after selling my 993 C4S years ago. I drove a coupe of 05 997 S (one with grey interior meh, another one a launch with PCCB). Interior and sport seats are great. Enough power for street and track.
Drove a 996 TT as well. It was modified for track and I wasn't a fan of the interior for the amount of money being spent. As for the 997 I am the type to worry so even after the IMS is done I would still worry about losing the motor to bore scoring. Boroscope is worth it on a car you are serious about it. The jump to 997.2 (09+) did not seem worth it to me. The 997.2 base Carrera is a good buy if you can find one at a reasonable price.
If you don't have back roads and will be stuck in traffic it may be time to go PDK. Cayman or Boxster are readily available.
As for me after driving 997.1 and 996 TT a friend offered me his 2011 BMW 1M (driver) for a reasonable price and I have been enjoying it since. Collectible, lively, RWD, 6spd manual, twin turbo, large enough back seats for kids.
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