The only timing chain "issues" that I've heard about are on this forum. In my neck of the woods, there's not many Challengers, but a TON of RAM Hemi's running around.
Most have lived a "hard life", and the owners really like them.
This alone helped me decide on the 5.7l motor as being a "good one".
Yes, anything can happen, and that's why I bought the Chysler Lifetime Bumper to Bumper warranty. The drivetrain has the normal 5/100 coverage, and after that, the extended takes over for $100 deduct.
I'm running mine as usual, and not losing any sleep over anything on the Challenger. It's covered, and it's been a great ride for over a year now and 16k + miles
2010 RT "Classic" Automatic
Options: (28M); Electronics Convenience Group; Power Sunroof; and the best $225 option in the world: Detonator Yellow Clear Coat
Mods: "R/T" headrests by Jina's,BT nose badge, Mopar front strut brace, Petty's rear strut brace, 4861940AC air tube, BT catch can, Mopar door sill plates, Mopar "T" handle shifter, Mopar Bright Pedals, Mopar "Dodge" center caps, R/T rear spoiler badge, Mopar HO carbon fiber engine cover, Mopar hood struts, tinted windows.