[Perfectlap]

In your situation, being that you already have a roadster, I would consider an air-cooled Carrera first. The SC's seem to be viewed as one of the more reliable ones long-term and their values continue to rise (if that matters to you) mainly because Porsche produced very limited numbers of air-cooled cars vs. the water cooled era of Boxsters/Caymans and 1999-2014 911's. The 964's are a bit more money but they are the last of the 911's with the high fenders and round headlights but are still considered modern Porsches with all the safety considerations. Being that you will probably put very few miles on the car it might be nice to sell the car at some point for more than you paid. If you plan to drive the car year round no matter the weather and do some track days and AX, and could care less about hiking up the odometer, then the water-cooled Porsches are probably the better option. If you wreck it or the engine lets go there are plenty of used ones around to replace it. I guess its up to you, do you want a show horse or a work horse.