I LOVE the suggestion of a raincape (I had to google it to see what it is, but now that I know...). In my experience riding in Saskatoon if it is raining a little bit, there is a good chance that it will soon be raining heavily, and I will get far wetter from the rain (even through my shell, which keeps out light rain) than from my perspiration.

The water bottle is fine strapped to the cage while I am riding, but it is afterwards that I was thinking about. But realizing that - when stopping at a store on my way home - I should still have water in it for the remainder of the ride, compactability becomes a moot point.

For any of the stuff, I would not feel comfortable leaving ANY of it on my bike outside for hours on end (or even a few minutes). I have little doubt that it would not take long before stuff just started walking away on me.

As far as the clothes I wear while riding, in the warmer weather I am not wearing anything specifically made for bicycling, but rather some active wear (not sure of the specifics) shorts and t-shirt from Old Navy.

The one thing that is looking to be a bit of a nuisance is the shoes. I would love to find something that doesn't take up a lot of space. At the moment, I am thinking of investigating Vibram FiveFingers, Sandals, and Water Shoes to see if there is anything that would be suitable. Basically something that takes up less space in my bag (I ride with riding shoes. I find if I do a lot of riding on non-riding shoes my feet start to hurt, so riding with my work shoes is out).