My sense was that bike transpo culture was much more robust in Osaka and Kyoto compared to Tokyo. If memory serves, there was TONS of sidewalk parking so no issues there(the subject of this post just seems inflammatory TBH) but also the sidewalks were quite a bit wider than what I'm used to in cities I've been to in the USA(like SF). Also, you don't really worry about your bike getting stolen on Osaka.

EDIT: Tokyo is ginormous though and I haven't really been on the ground in more than like 5 or so of the special wards :|