[Driven97]

The only way you're going to get the special feel of an air-cooled vintage car is to have one. You're not going to capture "something similar," nothing else is going to be the same.

That said, modern cars are objectively better. Quiet, comfortable, easy to drive, working A/C, easily much faster. A 997.2 is NOT going to be just like your car but newer, it's going to be totally different. As much as it pains me to agree with Sugarwood, if you decide you're willing to abandon your very unique vintage car, then just go ahead and open up your world of choices.

Maybe you end up keeping your car. Maybe you go to a 996 turbo, or a 981 Boxster S. Maybe you end up in a Twin or ND Miata. Maybe you cross over to an M2, M3, or M4. Maybe you go hardcore with an Alfa 4C, or go to the dark side with a Camaro SS 1LE or Corvette of some sort. Maybe you posh it up with an Aston V8 Vantage. All of those things are probably within your budget and within the possible spectrum of what you want out of a car. Test drive, test drive, test drive, and the right car is the one you can't stop thinking about.

Life is too short. Cars are far less permanent than wives (well, for most of us) you can swap as much as you want. The only real bummer is that once your 911 is gone, it's gone. You can get another air cooled car, but that one is yours.