Welcome to Carpokes!
20-years is quite a long time to be Porsche-less, so getting back in the game has to be exciting.
I suppose there are not too many wrong answers as to what you buy as long as it's either a super straight car or that you know what you're getting in to if it needs some tweaks or TLC. Most importantly in my mind is that it's one that pushes the right buttons for you.
Both the 997 and the 991 gens are excellent in my book for post-air-cooled 911s - great cars! I had a 991.2 Turbo that I loved and often wish I still had. What a great car.
It's hard for me to give anything but the most general advice, but I guess I'd spend time looking at auctions, sales, info from Stuttgart Market Letter, friends' Porsches, demo rides at dealers who might have models close to what you're looking for, etc.
Don't overlook the 981 and 982 Caymans while you're on the hunt. You've been there and know what fun cars they are and how well they drive. Speaking of 982s, there are lots of hard-core 718 fans here.
I'm sure others on Carpokes will have thoughts and opinions. Whatever journey you choose, have fun!
