I had dipped my toe into SF almost four years ago, then disappeared, then started lurking again when it was time for a new bag to replace my 6yo Wilson Leather satchel. Lots of good information here, and it was the really in-depth reviews that ultimately helped me out the most. Since I ended up getting a Saddleback, I figured I'd contribute my own review with the hopes that it might help someone else who's trying to pick a bag. Hopefully I attached the photos correctly... hover over them for descriptions.
First off, the Wilson. Generally it was perfect. The design was great and I ended up using each 'feature' and the build was great too. I had no zipper failures or anything like that. Ultimately it was the really low leather quality that spelled its doom, as it just started to fray and disintegrate and look like hell (not that it was ever anything special in the looks department). Note that I don't blame the bag or Wilson... this was a $100 bag that I bought in a mall and then proceeded to beat to shit every single day for six years; to and from work, on many plane rides, trips to the mountain house, camping trips, whatever. Any tool that I can get six great years out of for that price is something I end up appreciating. Good job, Wilson.
I settled on a Saddleback Large briefcase in coffee brown. I wanted a tool that would last me for the rest of my life, be super-functional, look great, be an everywhere/forever item. Sure the 100 year warranty is just marketing bull but with all the research I did, it seemed like the things are really built about as strong as something like this can be. The style matches my personality pretty well; all the similar bags in this price range or higher were too formal. While I'm serious business, I'm not persistently buttoned-down so this bag is a good fit.
Got it mid January and now we're about three months down the road. Here's my quarter-year brain dump.
Size: I'm 6 foot 4 inches, 215 pounds. The large is a totally appropriate size, although it apparently looks big-ish because my wife has teased me about taking a suitcase everywhere.
Capacity: I carry a lot of stuff with me every day (just finished up chairing a conference and my city's technical society chapter, got a big family with lots of stuff going on at all times, I've got a complicated job where I work from home after putting in a long day, etc etc). Lots of files, a netbook and cables, plaques, a large moleskine, mail, etc etc. I would have been screwed with anything smaller. I've done trips and put clothes in with the other stuff; this has been okay, but I suspect will be much improved once the bag loosens up (more on that below).
Flexibility: I could carry a similar load of stuff in the Wilson because it could unzip along its edge and expand, plus it was very soft and would blow way out when I crammed stuff in. The Saddleback, on the other hand, was less of a bag and more of a hardshell case when I bought it. Even three months later it's still mostly stiff as a board. I expect that once it's broken in I will see an increase in capacity, but hell that might be a year away. This thing is STIFF. Note that this is not a criticism; the leather is simply very very thick.
Looks: so dreamy. The color is wonderful, the contrast with the chrome hardware is beatiful, and the interior lining is really nice. I've gotten a range of comments, from "I like your satchel" to clearly lustful "that is a REALLY NICE BAG." Apparently the finish is designed to look beat up like as soon as possible, and that's kind of corny, but it's not a big deal as far as I'm concerned. I saw a photo where someone just cut to the chase and changed the finish a bit so that it looked less "chipped" but I'm too lazy for that, plus I don't care all that much.
Design: Thought I would struggle with the buckles a bit (the last bag had quick-release) but it's been zero issue. The straps don't necessarily fit all that well, but more on that later. I've had the shoulder strap clamp get bumped and release a few times, dropping one end of the bag. I'll probably tie those closed and that'll solve that.
The outside sheet pocket is appreciated, and the separation between the two main interior pockets is probably a good thing otherwise my netbook and stuff would clunk around in there since the bag is still effectively a hard case. I thought I would dislike the primitive open pockets but they haven't been as bad as I feared. They're deep enough, so everything stays in for the most part. If I slam on my brakes and the bag falls forward, then yeah I'm cleaning up coins and thumbdrives and eyedrop containers and stuff when I open it next. Not great for OCD organizers, of course. The exterior pockets are okay too; right now they're so stiff that I can jam my wallet in there with no fear, but when they loosen up then that's going to be a concern.
Someone mentioned once the idea of something like an ammo pouch that you could buy and attach to the strap; I would buy the HELL out of that as long as it was closeable, for the typical wallet-phone storage. The keystrap is nice. I actually use the external rings enough that I keep a carabiner clipped on at all times; that was a surprise too. I know some people have said that they'll never use them. Haven't used the backpack function yet but I know I will and am really happy to have that option available. I'm glad the logo is hidden by the flap; there's a lot of the Saddleback stuff I'll never buy because their logo is front-and-center.
I wish the interior center divider had a handhole; frequently I have the bag wide open and I want to move it, and it'd be really nice just to be able to grab it dead-center. I bet a lot of people would like this.
Weight: I read a lot about it being heavy, but I've been lugging so much stuff around for so long that I really didn't notice any difference. My daily kit weighs a ton, whether it's in the Saddleback or the Wilson heh.
Beefs: So, a few things I'm struggling with. First, for me since I have very big hands the handle/backpack ring attachment proximity is a real problem. The handle is super-stiff and doesn't stand all that far off the bag surface, and the ring attachment is really too close to the handle. I kind of have to shove my hand through to carry the bag and it's not great on the knuckles.
I'm having thread drama; not sure how much I should freak out about this but since I'm fairly OCD the broken or shredded threads really mess with my head.
The worst problems I have are when I want to cinch the bag down tight and it's not crammed full at full capacity. I can't think that this bag was really designed to be cinched down to a small size. First problem: when it's cinched, the handle comes around onto the face of the bag and now carrying it is super weird and awkward. WTF! Next, the way the two straps are threaded through the bag means they stay partially cinched even when unbuckled, pinching down that bag edge and making it impossible to keep standing on it's bottom. Perhaps this next thing will go away with years, but right now the edges are thicker than the middle and so the bag doesn't close down evenly. Finally, if you cinch it down much then the central strap can't be buckled since the strap locations, reinforcing loops, attachment points, and lengths are really only designed for the bag to be fully loaded. Oh, and the hidden compartment flap sticks straight up then too.
Summary: So all in all it's a great bag. Sure the design is a bit primitive once you actually start using it, but if the build quality is as high as is implied then this beautiful thing is worth every penny. Once it's completely soft I believe the usability will be a dramatic improvement over the new, stiff feel.
Questions are welcome.