6 speed if you are happy to travel slowly with luggage, 2 speed for that about town fixie feel.
I live on the top of a decently steep hill, so guessing the 6 speed?
Yes. Hills aren't great on the 2spd. If you're going 6spd might as well go dynamo too, as it won't be light.
Definitely 6 speed. 2 speed is 55/75gi ish. 6 is 33-105 ish.
@Dammit started
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6 speed if you are happy to travel slowly with luggage, 2 speed for that about town fixie feel.