sterling post mr. TJ, very well said. OP I'd lean towards to the mess bag because it sounds like you'll need it for the chaos factor. no1mad's seagull option looks like a good one. I can't tell you much about the strap because it's the only bag like it I've ever used. it's different than a backback, but it's not a backback. It's better than those one strap backpacks by a mile. I notice the seagull has a corner that sticks up a little. if your were in a tuck and looked behind you all you would see is the corner of your bag. if you get one, the right shoulder option my be best, for that blind spot alone.