Automobile Enthusiasts

Pros of the Classic Beetle:
Iconic
Fun to drive
Reasonably good on gas
Easy to work on

Cons of the Classic Beetle:
Nearly impossible to buy tires for the stupid thing...the tire size is 165R15. TireRack sells two models of tire for it. The cheap one costs $91 per tire and has a UTQG rating of 280. The other is a summer-only tire with a UTQG rating of 220, and it costs $128.20 per corner. (By way of comparison, you can buy a set of Continentals for a New Beetle with UTQG of 700 for $113 per tire.)
Parts are starting to get REAL expensive
The seats are horrid
"Crash protection" involves the car being so slow you can't get into much trouble
You're working on it all the time
Air conditioning is of the "245" variety, and if you want to be warm in the winter you need to wear a heavy coat

Pros of the New Beetle (with TDI engine and 5-speed manual transmission):
Slightly less iconic, but still fun
I hardly ever need to work on mine; YMMV.
Extremely good on fuel
Quicker than you'd think a diesel would be
The expensive bits are not all that expensive because they're shared with the Mk.IV Golf and Jetta

Cons of the New Beetle:
The design of the engine compartment is Germany's revenge on America for having lost two wars. There is just barely enough room in there to get components in and out, so work takes longer than it should because you're trying to thread things into place.