I'd say look for a nice 996 convertible.... I found a perfect, one owner, all service record, service done at the dealer, 5k in wear parts replaced, etc.... fully loaded to the brim from Porsche of Scottsdale in AZ for a price near your budget.
Just keep your eyes open, I loved my boxster, but I fell in love with the 996 after I test drove one.
Adam...
