Instead of trying to get emacs to work, maybe the right way to go about this is to try to learn how to script Outlook to do what I want.
With the quick investigation I’ve done into the matter, it should be too hard to write a script that does something similar to mew/wl’s refile mechanism using vbscript inside of outlook. Maybe if I get really motivated, I could throw a UI around it too.
In the end, these things are probably much better thought out in COM/MAPI land than emacs-lisp land.