For years Yale has had a free shuttle bus for community members to the "Grad Ghetto" part of town, which is great (though it would be nice if they'd fix the squeaky brakes!). However, the housing in the Orange St. area has gotten overpriced, and smug landlords don't bother keeping apartments repaired because they know that there will always be another grad student looking for a place to live near the shuttle line.
Why not have shuttle loops that go west (to the Yale Bowl/ Westville area) and east (to Fairview/ Wooster Sq.). This would(a) expand the housing stock that is available to grad students/ off-campus undergrads/ postdocs, much of it considerably cheaper than the grad ghetto;(b) make it easier for Yale workers to get to their jobs while putting more money in the pockets of those workers who take the city bus and cutting down on parking demands for those who drive;(c) make it easier for undergrads and others to get to the IM Fields for club sports;and (d) make great pizza more accessible to all Yalies.
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Combine this idea with ending the war on drugs, and the ghetto and crime of the area can end also... just a thought.