Car #2: 1965 Corvette Convertible (aka midyear C2)
Why? Well, first, I think the "C2" Corvette (1963-1967) is perhaps the most beautiful American car ever mass produced. Second, it's utterly different from the last car: American, naturally-aspirated 327 cu. in. (that's 5.3 liters) V8 engine in front, over 50 years old, made of fiberglass. It also meets my other criteria -- it's not losing value (probably gaining value!), parts and service are easy to find, and there's a great community behind it.
First impressions? It's LOUD. And it's completely different from driving the 37 years younger Porsche.