RE: why a Challenger?
Just as the '70 Challenger is still a desirable classic, the 2008 Challenger's destiny should be the same.
I bought a '70 Challenger new and drove it as my everyday car for 14 years. I did most all of my own maintenance and body work too. I had no trouble selling the vehicle to a local mechanic. I now buy used vehicles for my everyday transportation and really don't care to do the maintenace anymore.
I plan to buy and keep a 2008 Challenger and eventually leave it to my children. This will not be an everyday car, though. I'm looking for a vehicle to have fun with - local car shows, cruising nights, and possibly the Hot Rod Power Tour or other such events.
The quality built into today's cars along with the timeless styling of the Challenger makes me confident that I'll be driving my new "classic" for as long as I'm able to drive.
Good luck with your choice.