I too agree this is a fantastic idea. I've used the bike share programs in Minneapolis as well as Capital Bikeshare in Washington D.C. I think the best way to sell it to the city is to market it as increased revitalization to other areas of the city.
If you work downtown and want to grab lunch in the South Side or Station Square it'd be a quick bike ride over. If you want to eat on the North Shore it's a quick ride.
Now the hills in Oakland, Shadyside and Squirrel Hill might make a bikeshare in those areas more difficult, but downtown, the southside and the northside should easy to connect!
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If you work downtown and want to grab lunch in the South Side or Station Square it'd be a quick bike ride over. If you want to eat on the North Shore it's a quick ride.
Now the hills in Oakland, Shadyside and Squirrel Hill might make a bikeshare in those areas more difficult, but downtown, the southside and the northside should easy to connect!