A friend of mine has one, a non-"S" model. It looks good and its quick, but not crazy fast. Another friends 944 non-turbo actually feels faster.

The Boxster handles great but rides extremely rough, and the seats are slim. I like them, and used ones are dropping down in price to what is realistic for more people, like 25-30K. My friend paid 38K I think. The car totally fits my friend's image, though.

I would consider the 968 convertibles-still expensive to maintain but cheaper than a Boxster, much cheaper to obtain and quite good looking. A lot of people hate the 68, though.