Hi Kyle - I tried out this 'migration' process you described in my test environment and it seems to work BUT there is one issue......look at the following screendump:
the picture on the right hand side is a gallery image which has been created by the migration process (that means it existed already in the CB 1.9.1 environment before upgrading to CB 2.0.8 and before loading the CB Gallery plugin)...the picture on the left hand side was created after the migration via an upload of the user....as you can see the quality of the right picture is really bad (important: both pictures are based on the same original file).....is it possible that the rendering routing is not startet wenn the CB Gallery plugin is loaded?....because all the thumbnail pictures that were established by 'migration' have this bad quality....
regards Eric