I've got a Chrome Citizen. The bag is absolutely rock solid, but I wouldn't want to carry more than a 5 to 8 pound load in it for an hour of riding.

Your load looks to be far more than 5 to 8 pounds:

• textbook
• small book
• notebook
• gym clothes
• regular change of clothes
• an extra jacket
• lunch
• quick errands
• My helmet
• wherever else

I don't even think that the Citizen has enough volume to carry that much stuff. I think your load calls for more of a Metropolis sized bag.