New Challenger vs Original

If you keep it in good shape the old one will continue appreciate in value. (unless the bottom completely drops out of the market) The new one won't be worth what you paid for it for 25 years or so. The early small block cars are a blast to drive too.
Here's a shot of 4 cars owned by a couple friends of mine. They are brothers and got into collecting E-bodies a few years ago. These are all 340 cars and 3 have factory shakers. Lots of fun!