Hey guys. Long time lurker on here, first real post. So, let me start by saying I ride a mountain bike some days, ride my motorcycle some days, and sometimes walk, either around town or longer trips about 2 hours commuting to work.
I have read countless threads about picking the right bag, and I have learned a lot. But for the heck of it, I would love to hear some of your recent updated opinions on a few points for my next bag.
So, if you don't mind helping with some advise...
I am looking again for a bag, must be

messenger bag (already have tons of backpacks)
medium/large , could be an every day bag probably
Need for walking and riding! Top priority is comfort!!
I have a timbuk2 medium, and even light loads dig in pretty bad. I know a backpack is better, but this thread is more about finding the most comfortable mess bag.

I have looked at all the major ones, chrome, seagull, reload, bailey, etc. etc. etc.

So, as far as bring a skinny guy, I don't ever really need to carry huge bulky loads, more of a sweatshirt, sometimes laptop, books, type of stuff with the occasional odds and ends. Pockets are a plus, as is compression straps so I can flatten her down when only carrying a laptop or books on some days.

Money isn't really an issue, but comfort is, and aesthetics doesn't hurt either.
So, thanks for any advice that you guys have, that I probably haven't read in older threads. I do like the look of bailey works, reload, seagull, and chrome. So, thanks again, any help before I pull the plug on one of these is much appreciated.

Dave