It's really all about intended usage. If your daily drive involves a bit of interstate and you enjoy a spirited drive then the 996tt is utterly intoxicating ... once you go this route you will not be able to go back. This car makes BIG POWER and is capable of using it (as long as the driver is.) On the other hand there is nothing more frustrating then driving a super car in traffic. If you are really looking for a go-cart (i.e. the connected experience) then get a miata. The air cooled machines are just not part of the modern driving equation anymore, the relentless march of technology has simply moved on
Now if you are talking about collectibility, cool-factor, hipster credit ... then it's 993 all the way baby, but thats a topic for another thread