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Anonymous
Call me crazy, but my recommendation would be to go with a tiny rangefinder.
Alas, that was the era of film and not digital, so I'll say to stick with small primes, and try to be inconspicuous. Try not to take touristy pictures, as has already been said. A big ol' telephoto might turn people off, but if you keep your body fitted with a nice small prime (pancake would be best, but i'm not a big canon guy so i don't know if they have any), it'll be a little less unwelcome, partly because you have to get up close with it. Everyday settings and situations would work nicely. People going to work, lunchtime, etc.
In fact, I would try to stay away from the telephoto and stick with primes, but i've been called insane before, so take it with a grain of salt.
Can't help to think that the tiny Pentax ME or the more full-featured Olympus OM-1 would be fantastic in this situation. Small lenses, small, quiet cameras. Inconspicuous at its best.
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