Since I became active in OSM over the past 10 months or so, I look back and see a bit of progress in Cleveland that I made.
There's a quite a few neighborhoods that are done (I'm using done loosely here, as having all of its ways verified and named, if applicable, with the exception of less than handful of streets in each): Ohio City, Brooklyn Centre, Downtown Warehouse District, Tremont, Old Brooklyn, Hough, and Detroit-Shoreway.
In fact, most ways west of downtown to W.100th are done. The TIGER edited map viewer - http://open.mapquestapi.com/tigerviewer/index.html?zoom=12&lat=41.47058&lon=-81.70815&layers=B highlights what has been edited since the TIGER import.
Pretty much there's just West Park/Kamm's Corner, Collinwood, the flats, mount pleasant, a part of slavic village (I hope to take that out in the next week or 2), and the Lee/harvard are.
I've also been through a lot of parts of Cleveland that I wouldn't have visited otherwise, found a couple cool businesses, picturesque views, nice houses, some Cleveland history, and met a couple people.