If your looking at a supra, go for an aerotop SZ (not too sure on price, but am pretty sure they're around 15k).
I'm guessing the car will be your daily-driver, so I would say the newer the better, unless you don't mind little things going wrong.
Not really sure what you want, but maybe a e36 bmw?? Just a suggestion.
I'd personally go for
1) R34 N/A (r33's are too common now)
2) Supra (aerotop if possible)
3) Prelude Vti-r
4) E36 bmw (if you like them)
Good luck with your search mate.