I have the Chrome Citizen, special nite series (black with reflectivity). I paid $180 for it and liked it so much i bought another one for my brother. I use it every day on or off the bike. I take it to work with me as a briefcase. I find it to be very comfortable to ride around with this sort of stuff-- 2 tubes, couple of cliff bars, minitool, sweatshirt, gloves, sunblock, couple of eyeglasses/sunglasses,bike lights i can take on and off the bike easily, a planet bike rear light i can use on the bag itself, antiperspirant, tooth brush, toothpaste, floss, construction vest, some misc papers etc, paperback, newspaper. This all weighs maybe 4-5 pounds at most plus the bag. Id estimate total weight maybe 8-9 pounds. This is no problem at all. It is no burden to carry around. I do it all the time. What is too much for comfort is my 13" laptop computer and case and power supply added to the messenger bag. I have ridden 40 miles with this stuff on my back and its just about 8 pounds too much for comfort. So i recently got a rear rack installed on a bike, and ziptied a milk crate to the back and i put the Chrome bag in there. And i added a holder for a Big Gulp from 711 (in addition to 2 water bottle holders on the bike.) I am much happier with the weight off my back and in the crate when i have the laptop with me and i like to take that around to stop at wifi locations around town. I also like to be able to stop at 711's and get a refill on my Big gulp and stick it in my milk crate in the drink holder.

I dont think you could get any bag or backpack that is more comfortable or better at carrying weight than the Chrome Citizen. Chrome has 20 years experience improving this bag and it has excellent featuers and weight distribution. I was amazed how much more comfortable it is than my old laptop computer backpack that was sold by Sony. I have also walked around nyc with this chrome bag on my back with my laptop computer in it, and it isnt that bad. I can use it as an overnight bag or airplane /train carry on bag with my laptop computer it it and a small amount of other stuff, like a change of casual clothing.

But as many other people have said once you get in the area of 8-10 pounds of stuff in a bag then it is more comfortable to get it off your back and onto a bike rack or basket or crate. That is what i have learned over time. I was resistant getting a rack because i didnt know what to get, too many options with racks and panniers, and not cheap, and i have a few bikes so i didnt want to outfit them all so i stayed with my messenger bag too long with too much weight. I only got into a rack/milk crate by accident after buying n+1 bikes that came with a decent rack installed and i immediately zip tied a milk crate to it, so i can take my laptop around town off my back.