Kinda hard to figure out what you're looking for. That's prolly because
you haven't figured it out for yourself. No probs, it's a process, right?
Seems to me the first thing to do is create a list of cars you want, then create a list of things you want to do with a car. There doesn't have to be any sense or logic to this; just start jotting down what you want. I think after you have these two lists some commonalities will pop out at you. Whether you want to follow these clues or not is up to you. Its just a starting point.
One thing I noticed from the cars you listed was a sort of macho, hairy chest image thing. Except for the Beretta which I can't figure out why you bought that car.....

And the Benz doesn't really fit except for the "body builder in an Armani suit" image. But all the others project a vivid, extroverted, semi-tough guy street image. Since it's clear to me this is the style and image you want to project, why not stick with it? Seems this is the look that turns you on, right?
As for what cars to buy, its a lot easier on you and your wallet to stick with American cars like Mustangs, Camaros, Corvettes, etc. Lots of support, affordable, plenty of mechanics to do work you can't do, won't take you to the cleaners if you need major work. Old Jaguars can be money pits and need constant attention but provide a nice reward when all is well. Best thing to do with them is buy the best car possible instead of a fixer-upper. Ferraris are like this to but even more extreme. You really need deep pockets to keep them running their best. There's lots of support for moderns like Vettes and Mustangs and that usually depends on what you can afford to mod. There's also a sizeable aftermarket for BMW's, Audi's, and VW's.
I'd be interested to see what list of cars you come up with. It's always fascinating to hear from people why they're into a certain type of car. Keep us posted.