1) Tourists (the kind you can spot a mile away) look as astoundingly ridiculous as they do because these are people who only ever set foot inside a city when they are on vacation. As a result, they are completely unequipped to figure out what kind of gear would be practical in this environment, and instead substitute things that various catalog companies tell them will be practical and appropriate. Contrast with the gear and clothing of the city natives, which may appear impractical or even ridiculous and yet has not resulted in starvation or frostbite.
2) Any kind of usable reputation system has to find a good way to handle localized types of reputation. For example, I know enough people in the tech community in Portland that I can usually find someone to talk to at various events. Yet this is only useful in San Francisco if I ask someone I know in Portland for an introduction to someone here, or if I stalk my Twitter contacts aggressively.
3) I forgot what the third item was. Maybe something to do with blogging? Travel? Reasons I am not a rock star? (but that last one’s probably only funny to me at this point.)