Talked to a cohort of mine using this addon, which rules, and he's not having any issues with that. Will try a re-install again. I guess that would suggest one of my other addons is jacking with it. :-)
Yeah, sorry, I should have articulated that better. I click the x on the individual item and it removes it from the list for that moment. I then close omail (X in the top right) and type /omail again to open it back up and the items I previously removed prior to closing and re-opening are back on the listing and it sends that item there.