Depends on what you want out of it. Since I have both, I'll tell you how I feel about it.
• The classic is my hobby, obsession, toy whatever. It was my daily driver in college, and is never getting sold.
• The 96 is a car. Right now it happens to be a better daily driver than the 66, but that is changing.
When it comes to 94-98s, you are looking at cars from 6-10 years old and you are limited to pretty regular used GT's by your budget, so a low milage Cobra or something like that is likely out of the question. Not what I would call super reliable or very exciting. If you were considering a newer car (less than 3 years) there would be an argument for that since you would have something that you basically wouldn't have to work on for quite a while. Since that isn't the case, I would go for the best classic you can find. Preferrably a fastback simply because now that you've had one, a coupe is probably never going to fell like it's good enough.
JMO, of course.