I'm pretty sure my workflow will get really simple with the building blocks already in place and whatever Devs come up with in over the next few months. Specifically, I expect Hazel from Noodlesoft will solve the autotagging issue by giving official support for tags. I should be able to use this strategy auto tagging with Hazel. Also, Clark's Tech Blog indicates there should be some quick scripts to move my open meta tags to the new system tags here. Tack Quicksilver on top and I think I should be good to go!