How are older cars "maintenance heavy" compared to newer ones? When was the last time you had to spend days chasing down a Check Engine Light problem on a Road Runner? When was the last time you had a failed injector on a Fury? When was the last time you had a no-start due to a bad CPS on a 440? When was the last time you had to spend five hours dismantling most of the top end of the engine to change out a bolt-on part on a 440? And as my favorite parts guy once told his co-worker, "when was the last time you sold someone a computer for their car for $20?"

My road runner needs three things to run: gas, air, and spark, and a failure of any three of these can be troubleshot at home and in quick order. One of my newer cars fails to start, whoa boy.
I remember back in 1991 I was driving a 73 Road Runner and beat a Ferrari 308 GTi coming out of four red lights. I stopped at a shopping center and the Ferrari owner pulled up and said "yeah, you can beat me in acceleration but there's no way you would beat me in the curves", to which I responded "First, where do you see any twisting, windy, roads around here? The only curves we have are the on and off ramps to I-95. Second, your car cost $80,000. Mine cost $1,700. Give me one half what you paid for your car and I'll have my car ready to take you on the curviest road you can find!" Now I look at this discussion and my mindset hasn't changed much. I can't remember the last time I ever drove my 74 Road Runner on anything but roads with mild curves that any car can handle, and I'm going to be into my car for a little over $8,000 once my 440 is in there. So why would I ever want t blow $30K on a new Challenger?
Plus there's the big difference now one has mentioned yet... there are thousands and thousands of new hemi-powered cars out there, including Chargers and Challengers. No one really notices them anymore. You jump in a vintage Mopar with those 440 or 426 Hemi badges... you definitely get peoples' attention.