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I have a self admitted bag fetish. I have used most of the tacticool and outdoor brands out there. 5.11 is my least favorite of any of them due to construction. Tactical Tailor is probably the best, for tactical usage. If you were looking for a full size pack - I would steer you towards Kirafu, but they don't make a messenger bag. Maxpedition is ok, but always left me with a "meh" reaction every time I handle their products. Others use and love them, so I seem to be in the minority.

When it comes to messenger style bags, I think the outdoor guys get the nod for everyday usage, carrying guns/mags/cuffs secretly, and holding up to wear/tear. 2 out of 3 favorites are made by outdoor companies.

The three bags in that style get the most use in my collection are as follows:

A Mountainsmith Lumbar Pack like this: http://mountainsmith.com/index.php/lumb ... ft-fx.html" onclick="window.open(this.href);return false; - Mine is older and discontinued, but Mountainsmith replaced a buckle that I slammed in the trunk and broke for free. I use this one to carry workout clothes, and uniform clothes (black Under Armor etc) to/from work. Had it the longest, and I love it. Priced around $50-$70

A Timbuk2 messenger bag. Made popular by cyclists, before the baby I used this on wet weather days to/from school as it is weatherproof. Post baby, it has been seized and converted to diaperbag duty as it is one that I don't mind toting around, and matches our high falootin' stroller, carseat, baby carrier. That's life. These are around $60, I think I have a medium one. http://www.timbuk2.com/tb2/" onclick="window.open(this.href);return false;

For commuting to school and flight travel, I mostly use a leather messenger bag from Banana Republic. It was pricey but was a gift from the wife when I got readmitted to finish my engineering degree a few years back while I was working full time. It has held up splendidly, and I love it. I think they are around $250 new. Here is a googled link I found of my model - http://s1070.beta.photobucket.com/user/ ... 1.jpg.html" onclick="window.open(this.href);return false;

I know those aren't the comparison's you were looking for, but I think they would serve you well.