Sorry to keep posting here, don't mean to overpost...but...what do you want this car to do? You have no cash to put into it once you get it...your probably not going to race it or autocross it or anything...you've got the Millinia....what do you want a car to do?
I can second the Z-28 or Mustang thing, but remember that Gas may well go to $4.00 plus per gallon, and your not really a CEO at this point....
The older W body Cutlass thing has me thinking pleasant thoughts, but there are lots of abused 15 year old cars out there so be careful...
The Rear wheel drive Cutlass/Monte is where I would put my money. We have a customer we do electrical work for and he buys and sells cars on the side. He says the hottest car on the bottom end of the market right now is the older RWD Cutlass/Monte.
Look at it this way....with that platform the car can do whatever you want. Drag car, Low Rider, boulevard cruiser, full custom, nice stocker for a sunday driver, dirt track stock car, short track stock car, whatever you want these cars do it all.
This is the one platform that you can afford right now that will go up in value (probably) be affordable to restore/modify, etc.
Good, solid cars can still be found for under two grand if you look, and I have a friend that buys and sells the mid 80's Monte SS cars if you need help finding the right car.
Plus these cars can be made into great freeway cruisers. With the right shocks and tires they ride well on long trips.
I still like the idea of a Miata, but look at it this way...
A friend of mine who is into Porsche' says that any Porsche is a 20 thousand dollar car once it is finally sorted.
Any Miata once it is really sorted out and everything is right is probably honestly a 5,000-6,000 car min, although you can buy a decent starting point for $3500-$4500 like I said.
Were I to be you I'd be looking for a better Cutlass or a Monte.
As for newer, I actually like Dodgefan's Idea of a Second gen Neon. reliable, roomy, really decent handeling car, won't ride quite as well as the Cutlass/Monte but will like to turn much better.
Or just become a Porn Star and buy that Viper after all.
Chris