The answer to question one is NO "modern" vehicle comes close to the old K5's as far as styling and utility,durability...todays tupperware trucks are not even trucks any more,they have sissified them too much with IFS and cushy interiors...more like caddilacs with an 8 foot bed than trucks..
I wish GM had some cahonies and build a few "retro" vehicles,and yeah,not the HHR's,what a POS those things are,they were just a copycat move to compete with the PT Cruiser (another POS,its just a Neon with a somewhat cool looking body slapped on it)...the other thing GM made that looks like an old Studebaker truck looks cool,but is useless as far as hauling anything...
They should bring back the first and second generation pickups and K5's,maybe upgrade them to 4 wheel discs and keep solid axles under them,the 14 bolt being the smallest available option!..with a newer V8 or a inline diesel drivetrain (Like the big Isuzu box trucks used that some have put in older GM trucks with good results) would be cool...
I bet a lot of older customers like myself wouldn't mind a plain old 350 with a 4 bbl being under the hood either...the new 6 speed manuals and automatics would be a nice upgrade...
Maybe I'm just nostalgic,but I wish we could walk into a GM dealer and plop down some cash,and drive off in a "brand new" 1969 GTO, a Chevelle SS 454,or a 70's vintage K5...I bet they would be surprised at how many they'ed sell....