Asks for rwd and fun, not diesel, gets derv Volvo soft roader suggestion. Good work, SXOC
Tbh 350 does seem to fit your wants. If you dropped the convertible dislike then I'd suggest an s2k as it does everything else you're after.
Rwd only rules out a lot of things unfortunately. Run of the mill Beemers are not fun cars, and a 5k e46 m3 should be avoided like the plague.
Hawkeye Scoobies are vaguely in budget aren't they?
Older s3s as well, but they won't exactly excite.
If you wanted to go more the way of cruisy but with a stupid engine, then the twin turbo v12 Merc CLs are nearly in reach. Magnificent engines, but I wouldn't advise one of you're already stretching to buy the car, as they'll likely empty your wallet even faster than they empty the tank.