While it's not a drop-top, you can get yourself into a Ferrari 308 or 328 for $30-40k.  Apart from the potential repair bills, I wouldn't be *too* worried about driving it, either.  Seems like they don't go down in value much, even for those few out there with 100k+ miles.  Of course, if you're used to Porsche repair bills, then Ferrari repair costs won't seem *that* much worse.