My roadwarrior bag:

Summary: High quality, distinctive and elegant, flexible, carry on, roller.

More details:
1. Very durable
2. Excellent stitching quality especially around handles
3. easy, smooth zippers and zip handles
4. lots of pockets everywhere. At least two in the front that I can bend down and access independently while on the move.
5. one mesh pocket (stretchable) for carrying water
6. strong, non-rickety handle
7. good quality smooth wheels
8. If I am spending upwards of $200, I'd like it to have a distinctive, elegant look (including maybe an inbuilt sound track that croons 'Oooh yeah' randomly much to the surprise of other folks - okay I was kidding here)
9. I'd like it to be expandable but only if required (via zips, for example)
10. must have a dedicated space for a laptop (upto 13 in)
11. If its a garment bag, I'd love to be able to reach in and get a few things out - maybe some innovative waterproof zip linings on the side? Right now, a garment bag needs to be opened up completely to access.
12. The quality and elegance of the bag should reflect not only on the outside but the inside as well (pay attention to small details - no clumsy screws, knobs, rusted metal hidden behind cloth, frayed plastic etc)

The inbuilt charging stuff, GPS, removable wheels etc - all seem like more trouble than its worth, to me.