Thanks for all the suggestions. I'm at my mother's place and stuck on dial-up so I didn't really check up on this thread for a while...
First, I'm not looking at a car as an appreciating investment, I would just like to get one that keeps its value if it's used as intended. Yes, I know that maintenance will be a factor but it will be a factor with a new car as well so I am not taking into account that particular cost.
Location-wise, that is a bit of an issue that will be hopefully resolved by March/April - my wife lives in Nevada so I'm looking to move out there, but that depends if I get a telecommuting job that I've been looking at. If I don't, we might have to move. And that might well mean Chicago. In that case, the 'classic daily driver' goes out of the window straight away.
I'd love the idea of a Fulvia Zagato but that would be a weekend car for me...
MGBs - had a GT, kinda liked it, probably wouldn't be able to resist the urge to modify it and I'm not sure howw well that would work as a daily driver afterwards.
I've been considering C4 vettes, possibly even a C3 but I think I'd be happier with a C4. If the job situation works out in my favour, driving a Miata for a year might allow me to buy a C4 ZR-1.
Andy, I assume you are thinking about the 'boat tail' Duetto? That would certainly wet my appetite. 911s - well, I do like them but I'm not sure that I can stand a convertible all the time due to the additional wind noise. Regarding the XKE - what sort of condition are we talking about? I think I can get one of those past the wife .
As to Volvos, yes a P1800 might fit the bill - coupe though, I don't like the looks of the ES much.
Keep them coming please, I do apprciate the suggestions.