Don't get me wrong, I like the platform and think our trucks hold up well over the long haul... But, I think anyone will agree, they are now an aging fleet of vehicles, shown not only in the absence of some of the today's comfort features and technologies but in the overall sheet metal design. I don't mind driving a vehicle engineered out of the late 90's, but some people do. And I don't deny being a "part-time" enthusist with the platform (countless members on here who would claim full-time afishionado status). But I highly doubt those in the market for a late model "high end" SUV are looking at any 360. Even the wife of corporate executive would be inclined to snatch up a Lincoln Nav or a M class Mercedes way before a fleet 360. A quick drive to the used car lots will tell you that TB/Envoy's/Rainiers/97x's are as common as Chrysler's minivans were back in the late 1980's. A 2008 Tahoe holds much more value (and interest) than any similar 08 Envoy Denali or Saab 97x.
Case in point, I've had my 06 Rainier for 3.5 years now, paid 16K for it with 29K miles on the dash. If I were in the market for another SUV, I would definitely not spend 20K (or even 16K) on GMT360. For a few thousand more, a similarily equiped Tahoe or Yukon would be my truck of choice. Now, however, if I were looking for a winter-friendly daily driver that would have potential for offroad use, hand's down a 4x4 360. But again, the purchase price would have to reflect the vehicle's age.