[Z-man]

Shaun:
Just realized you're from MA - have you considered a Subaru? Granted, it's not what you'd consider a 'vintage' or a 'cool' car, but they are very, very dependable and with AWD, you won't have problems in the winters.

The Subbie XT was a different looking car, and the SVX was a terrific grand touring car. (But the Flat Six in the SVX won't be a gas sipper...) Even the Loyale or an older Legacy would do the trick for you.

I would also think a VW GTi or Jetta would work for you as well.

If you want something with a little flash, consider the Toyota MR2 - 1st and 2nd gen, although the 2nd gen cars are still running above $3k, more or less.

I doubt that an older VW / Porsche / MG / Fiat would do well in the harsh winters - rust would be a major factor. If you were just looking to run the car in the summer, that's a different story.
- Z