[Cajundaddy]

Get what you want. People buy these cars for many different reasons and one probably suits your lifestyle better than another. There are no wrong answers here, just the best suited car for your needs and wants.

The 964 is a great car and will likely hold it's value pretty well over time. They are more finicky and have old school suspension compared with a more modern car but it is a nod to the past and pretty fun to drive.

996 is not my favorite Porsche style wise but they are a lotta car for the $$ right now. There are a handful of model specific issues that must be addressed but they are a modern appliance with A/C that works great.

My current favorite models in terms modern convenience, performance and bang for the $$ is the 997.2 and 987.2 (2009-2012). I don't expect to see the kind of appreciation in value as air cooled cars but for a bulletproof, high performance, comfortable ride with zero issues they are hard to beat. $30k buys an awful lot of car with these right now.