I completely understand your position on making the change. It's the main reason I have my Challenger today. I've owned some very fast cars in my day (I'm only 41 now), and could have easily went with a car that was quicker and faster than the Challenger. The two I was seriously considering were an '07-'09 GT500. Or, an '06-'08 Z06. Both cars have stellar performance, great looks, and keen attributes. But, both also lacked a good bit, in their own ways, what I wanted for a true daily-driven, year-round vehicle that could actually seat more than two, semi comfortably. Even when it came down to the Camaro SS, or a GT 5.0. Both lacked things I wanted and needed. And, even more importantly the room and comfort I wanted. And, yes. As you said, there will always be faster cars on the road. Even closer to home is the fact that you can always make any car faster. All it takes is the right parts and money. But, you better start off with a platform that comes as close to encompassing all that you want in a vehicle, because some things you just can change. Such as, interior room, trunk space, visibility, seating, etc. And, in some cases even looks. The Challenger lacks nothing in external appearance. There's really not one line, or curve that isn't appealing. When it comes to the visuals of some of it's competition, it seems there's many features that are hit, or miss with the world, and their respected, loyal fan bases. One of the only real negatives about the Challenger is it's weight. I can live with that. Because, it's that heft that makes the car so awesome, and comfortable as a daily ride. I've taken my Challenger on numerous road trips, including one that totaled over 4000 miles. I even did this with the SRT8 Chargers I had before it. It's the only car (as wells as the Chargers) that after thousands of miles of driving, I still felt refreshed like day one, where I could keep going for thousands of more miles, if the trip continued.
Good luck on your sale/trade/Challenger purchase. If money's no object. And, you drive a new 392 car. You'll be hooked, and the previous year cars, as well as models will simply be second best to you. However, if you're looking for a killer deal, and keeping to a certain budget, there are some outstanding deals to be had. Now, short of the 392 cars, I would suggest you drive both the R/T, and SRT8 Challenger models. Because, even though the R/T is a stout performer, especially with some bolt-ons (all '09 and up R/Ts have the "new" 5.7 HEMI with Eagle heads, VVT/VCT, and active intakes, which bring it's performance level real close to the SRT8) you need to check out the differences in the handling, braking, ride, additional amenities (if they matter), etc. True, you can add all of that later. But, depending on the deal you can find, you may want to start off ahead of the game from the start. Regardless, with any Challenger model you can really go wrong. Post up you progress in your dealings, as well as pics when you finally get your Challenger... Good luck..