360 vs 383

I'm not a quarter mile guy. I never paid attention to my friends Road Runner. You know, back in the day anything in the 13's was considered fast. Drag racing is best done with a car set up to only drag race and goes to the track on a trailer. A street car is a whole different car. You can do either with both cars, but neither will be good at both. I grew up with passing on a 2 lane road. I liked to wind it up to 3,000 rpm, wait for an opening, and floor it. I would be around someone in a heart beat or two and be back in my own lane. Never really picked a race, but never turned one down unless it looked dangerous or stupid. I always turned someone down at least twice. More of a traveling down the highway and some one would not let you alone. Then I would let it unwind. Always just walked away from any one who tried. Then they would leave you alone and I could go back to cruising down the highway.

As for the 68 Satellite with a stock 383, it would depend on what motor was in there and who tuned it. The only B-Body I ever owned was a 64 Polara with a Poly 318 and a push button 727. From there it was a 64 Barracuda with a 273 and 4 speed when I was 19. It was stock for a couple months. I had that car for about 20+ years.
I think either can be "good" at both, but not "great". But I get what you're saying. Each has compromises.