I can semi-answer questions 2 and 3...question 2 you already seem to have figured out. I can't think of anything else you'd need to bring other than either a co2 pump or a frame pump so you can inflate the extra innertube in case of a flat. And question 3...there is an advantage to wearing bike shorts with a pad on the butt as opposed to regular jogging shorts because on a long ride the saddle will really start to hurt if you don't have some sort of padding. I can't speak for a jersery though, I just ride in a t shirt and its just fine for me. I guess wearing a jersey depends on whether you want to wick sweat or not and also the look you are going for. I don't care about having the full blown cyclist look and I don't care if my clothes wick away sweat so a t shirt works for me.