Wow Ken, reading that routine, I totally want a picture taken now haha.

Rusty, dont worry about it, remember confidence is key! Also it might be easier to photograph certain people who are already dressed the part to stand out and attract attention. I find those folks usually would like to chat and that always opens it to asking for a photo. Parades and festivals are a good jumping off point as well, not just waiting on the sidelines, but if you are at the start or finish you can get some great snaps and chat up the groups of people there, and they are always game for a photo, especially one on film!