I’ve had 3 Timbuk2 bags and 1 Bagaboo. All have had loads of pockets, cross straps, strap pads and a lot of use.
I’ve got a Deedog (medium) from 1996 that’s still going strong. It’s been a school bag, uni bag, commuting bag, weekend away bag and has been hand luggage too. I’ve abused it massively, used it on and off the bike regularly and it’s only now showing signs of age with the liner cracking and the Velcro starting to come unstitched (which Timbuk2 have sent me some more of, for free). I’d like to retire it but Can’t stop using it!
I used to have an XL Timbuk2 that I got custom made, which was a travel bag and served as a courier bag for 12 months. I could fit all sorts in it, including a motorcycle helmet, a couple of suits, lots of packages, most of an A3 portfolio and lots of other stuff I’ve forgotten. I only sold it because it was too massive and I wasn’t using it.
I have a couple of years old small deluxe Timbuk2 which is big enough to fit a 13″ laptop in the decidated sleeve, plus enough stuff for a day out, or a weekend away if you don’t take lots of clothes. It looks like new.
And finally, I have a large Bagaboo which was a custom order. It’s of heavier duty construction than the Timbuk2 bags and was a similar price to my XL Timbuk2. The strap buckle’s not as easy to use but it’s a great bag that I tend to use as a travel bag since it’s a bit big for my day to day stuff.
I don’t have any experience of other brands but I’d recommend Timbuk2 and Bagaboo both for quality and usability, as well as how good their customer service is.