I don't know how old you are or what your favorite car is now or was as a child, but my advice to you is to find the fun car that REALLY tugs at the heart strings, no matter what age, and buy it if you can afford it. You will have no regrets. It might be today's latest exotic or yesteryears daily driver. It doesn't matter how old it is. What matters is how you feel when you drive it.
A little over 2 years ago I purchased my Challenger, it is a 2010 R/T. I told the dealer I wanted the Hemi and the 6-speed manual and didn't care about anything else and that's exactly what I got. I bought it because:
a.) I'm from the Detroit area, cars are kind of what we do.
b.) My Dad spent 37 years working in Chrysler engineering, this was the last car he worked on.
c.) My company does the exhaust for the vehicle and I had followed it since Day 1 in development.
d.) It looks amazing.
I know that it is the slowest of the 3 pony cars, and that it doesn't sell as well as the Mustang or the Camaro, but that doesn't change the fact that when I get in that driver's seat after an afternoon of detailing it and fire up that V-8 to take my wife out on the town - I feel like a million bucks. No other car has that for me, and that's why I bought mine. I picked up a beater to drive during the Michigan winter's and on rainy days and when I hate driving that thin I just think about what is sitting at home in the garage and it makes everything better.
Every Sunday night in the town I live in, they close down a block in downtown and people come in and park their classics and let people walk around and ask questions and enjoy. And everytime we go down there, I point to one of those and tell my wife "That's going to be us in 25 years."
So my long story aside, don't worry about the maintenance, pick the one you would rather drive on a night on the town, and you can't go wrong.
Last point: Buy it. AND DRIVE IT! I don't get total garage queens. I don't want mine exposed to the elements so it lasts. I have a rule, if it's over 20% chance of rain it stays in the garage, otherwise, it gets driven.
Like a wise men once said: "Find what you like and use it often

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