Weird Groove on Converter snout/bad leak

I know the bell was tight to the Block because it was a bear to get unbolted, but it very well could be a bad bushing. Im taking both the tranny and converter to a shop tomorrow, i dont know that ill go to the guys that built the tranny because i know they are good builders but they dont build converters like another place I know.
Just when I thought this was going to be a quick/cheap fix to get me back on the road now that the weather is finally getting better up here!
Is it possible for the bushing to go bad in only a couple thousand miles? Maybe the 904 isn't enough tranny for my motor? Its a healthy 360 that gets its neck rang quite often by my heavy right foot...

Thanks