Usage: I could not take the Charger on any 'must get there' journeys. So it got used 2-3 times a week most weeks; the Challenger can be and is used anytime. IMO you can't use a 60s car whenever you want unless you have great mechanical knowledge and a lot of spares....I had not much of the former and a lot of the latter.
Running costs: totally irrelevent if you can afford a Hellcat (but insurance cheaper for the Charger, also no VEL, fuel the same).
Character (and this for some IS THE THING about American cars): Charger wins by a mile....the smell, the styling, the sound. But I had to drive it to its and my limitations. With the Challenger going fast feels easy, with the Charger it was more involving.
If I could have afforded to keep both I would have because they are a totally different experience to me, but use them both for their own ends. I couldn't keep both so practicality has won out.
Final thought....how often can you use that 707HP? In Cornwall I run out of road well before the SRT8 runs out of go. It gets stretched on long runs and the annual Nats trip but otherwise????
...and Miles will certainly give it a work out down the track for you