Retro car experiments here in the US have been piss-poor by most standards, short of the forthcoming Camaro rebirth.
The Challenger -
-Too big
-Horrible interior (as with any Chrysler vehicle)
-Too pricey (original pony-cars were very affordable, designed to be cheaper than the hi-po big cube musclecars of the day.)
Mustang
-Horrible interior build quality
-Live rear axle???? WTF??
-option stacking killed this one (no "base" interior trim with V8, and 5spd)
PT Cruiser
-Missed age target by 20 years
-Retirement home hit
-Really bad interior ergonomics
Chevy HHR
-Um...the PT Cruiser failed...and you do this?
-Typical GM interior with no fit and finish, repeat of PT's mistakes (even down to the clock and window switches)
-Based off the failed and dead Cavalier platform
As for Chrysler "pushing the envelope", they hardly pushed anything - other than buyers out of the showrooms. Build quality never really recovered from the 80's, and transmission problems plagued the company, along with far too many platforms. A failing company doesn't need 609798686 platformed SUV clones. Their designs never really struck a cord with anyones feelings either, and barring the Viper (which is a brutally fast, yet shoddily built pile of crap) - nothing they make has any sort of brand image or soul.
GM is turning things around, and while they still need to trim some fat off the lineup - they will definately come out ontop of the big three when the smoke clears. Their new Sigma platform (Enclave,Aspen,Outlook,etc) is a huge jump from crappy rental-car-ready mid-size crossovers. The new Torrent effectively makes the old Trailblazer useless, and a fully optioned GMC Acadia would make any Q7/X5/RX owner blush.