I’m not one who has had the best Porsche cars (my dream car remains a gt3) but I’ve had some decent ones and can maybe lend a first timer perspective

cars I’ve had:
2001 boxster s manual
1999 996 cab tiptronic
Gt4

now have 964 c2 and 993 c2

996 was actually quite fun at road America and super nice cruiser. Felt more mature than the boxster. It’s a far better car than you’d imagine from the love for every other version of the 911. But for a while it will remain the “oh, it’s a 996 911.”

964 and 993 offer a sense of occasion but maybe not worth the extra cost and uneasiness if you don’t care about the whole air cooled purity bla bla bla thing

Gt4 was great but sterile and needed more power for its capabilities

For your budget I’d recommend a 2009 or newer cayman or boxster s

For a bit more $ a 997.2 carrera

944, 928, 968 are cool cars but aren’t going to offer anything unique and may get real boring real soon, you might as well get a vette or an m coupe

A 928 might be a good fit if you’re 6’7”, plenty of legroom in them and a wider cabin. They’re somewhat complicated but not overly complicated like the newer Porsche’s so you can still work on them.

If you go for a 997.1 you should consider changing out the IMS bearing and also make sure to have the engine scoped for bore scoring.

Good luck with your search.

this common refrain assumes the air cooled differentiation is the only meaningful difference