|Latitude: (41.4834, Longitude: -81.675|
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Cleveland is a city in Ohio at latitude 41° 29′ 0″ North, longitude 81° 40′ 30″ West.
Things that have been mapped relatively well:
The University Circle neighborhood (including the CWRU campus) by [SomeoneCallAlejandro]
Legacy Village mall
The Towpath Trail
Things to map
So much still left to map !
A couple neighborhoods [Old Brooklyn, St. Vincent's Charity Hospital's campus, Downtown, Ohio City, Kamm's Corner] are relatively more edited than other areas within Cleveland.
The suburbs (except in lake county) have had very minimal editing to them since the TIGER import. Suburban roads created since 2005 are likely not to be on the map !
Amenities including Churches, schools, Parks, cemeteries, and Post offices were added during the GNIS Import. Most of them (especially ones outside the city of Cleveland) are represented as nodes instead of ways and are often incorrectly placed on the map a few hundred feet from their actual locations. Some of these have since closed or changed names.
The CSU college campus is very sparsely mapped.
Innerbelt / Outdated Imagery / GPS traces
Significant construction to the I-90 bridge that runs through the southern end of downtown Cleveland, known locally as the Innerbelt is being reconstructed from 2011-2016. As a result, GPS traces and aerial imagery do not match what is currently on the ground and mapped.
There is also extensive construction in parts of Cleveland - Flats East Bank project, Medical Mart, Cleveland State Campus, the Mall renovation) occurring in Downtown Cleveland and the University Circle neighborhood so even the new bing imagery may not match what is really there.
Currently, it is generally recommended to use Bing imagery.
the aerial imagery from Bing in the city of Cleveland from lower zoom level until level 17 or 18 was taken in early 2012. Very high zoom level more detailed zoom levels contain imagery from Summer 2009. In both sources, there is a minimal offset (less than 3meters).
You don't need to align any imagery. The mapquest and NAIP imagery is from 2008 and its resolutions is lower than bing's. MapBox satellite imagery is a lower resolution than Bing and is from June-Sept. 2011.
OSM in the Community
There's the Open Geo Cleveland Group ! Meets bi-monthly and focuses on all things mappy and GIS in the open world which naturally includes OpenStreetMap !
The Cleveland Civic Hacking group graciously lets Open Geo Cleveland post our events under their meetup page.
Contact [skorasaurus] for more information.
October 19 - OSM Fall Edit-a-Thon 
April 20 - OSM Edit-a-thon - Recap
March 18th - Meetup event page
past Before regrouping and merging to become Open Geo Cleveland, there were a couple informal OSM meetings in April and August 2012.