I guess we all have this same type of dreams, only last time we ran this scenario with my friends we used a 500K budget instead. I've added nice pictures of each just to give the post some more texture. Here's my list:
50's - Citroen DS
60's - Jaguar E-Type
70's - Alfa Romeo Giulia Sprint GTV
80's - E28 BMW M5
90's - Honda NSX
00's - Aston Martin DB9
Do you blow it all on a Gullwing and an F40 and put up with a VW Golf...? Do you choose collectability? investment value? fun to drive? race history? rarity? Any cash left over goes to charity....
My selection criteria will probably differ from most here. I normally tend to fantasize about cars that I "could have bought" with my current level of income if I'd been my age and had my current job back in the day (except for the E-Type I must admit)... still very cool cars in my opinion. As for the more modern cars, I guess it really doesn't hurt to dream a bit, especially today when the difference between a really nice car and a DB9 is so big! Still, I'd probaly be giving a lot of that money away to charity as my selection is pretty modest.
I always go for cars that are fun to drive and that make people wonder what was going on in the mind of the designer when working on the car. Love cars that stand out for being ahead of their time, innovative or just insanely beautiful.
Andres G