As much as i love old muscle cars.
It sounds like you need a car to drive around in and have much more relaiable.
That new charger will start up every day, and won't give you much trouble at all. It can be warm cold, hot out, and it will start. The ac will blow cold, it will be comfterable, you can drive on the highway and set the cruise. And honestly, it's still fast.
If your lookign for a good weekend cruiser, somethign to take to car shows, possibly some drag racing, and somethign to tinker with get the old one, but beware it will be expensive by the time your done. It's worth it if you are a car guy, but if you don't have a lot of mechanical experience, get the new one, you'll be much happier in the end with a car just as fast, that acctually handles well.