Aaron Renn at The Urbanophile occupies a really important junction in the blogosphere, and I wish he had more company there. He loves transit but he's interested in all aspects of urban development and policy, so he tends to place transit issues in the larger context of a city's politics, especially conversations about civic identity. He writes mostly on Midwestern US cities, venturing to California only to prophesy its doom. But he has a good grasp of national and global peers and often draws on them for inspiration.
He's just completed a series on the transit challenges facing Chicago, but his descriptions of the political challenge are true of many cities. It's not about the technical or network planning issues -- for those I rely on The Transport Politic -- but he does deal with how transit proposals connect, or fail to connect, with fundamental desires of both the business booster and the average citizen.
Check it out. There's even some sex.