I don't understand why people think convertibles are extravagent or spendypants or anything. Until 2008 you could get a Camry convertible. Can still get a Chrysler 200 convertible, which is just a Dodge Avenger or Mitsubishi Lancer (boring, practical car). Mini Coopers, at least 2 current VW's, Mustangs and Camaro's (which are really not spendypants cars, especially in V6 form), and the Fiat are all "practical" convertibles as well, and none of them are fancy or all that expensive. Buick has one coming soon too. Why are they spendy pants?
On the sportier side of it, the S2000 is a great investment (seriously! No, it isn't VTSMX). I drove a Miata hard for 4 years and 60,000 miles and sold it for about $3,500 less than we paid for it. Not too bad, all things considered--less than $1000 a year in depreciation, and a lot of mileage on there. Corvettes don't depreciate that much if you take care of them and don't pile on miles...
I just don't understand the stuck up rich person stigma associated with a convertible.