This doesn't fix everything, but it improves things so it only takes a few commands to prep a fresh vagrant box to run the migrate_to_kuma_wiki command. I filed https://bugzilla.mozilla.org/show_bug.cgi?id=748806 for the rest.
*some* fixes for migrations for fresh vagrant boxes
Nuking my vagrant box again this morning to try this out
Works for me, with a second vagrant provision after the first vagrant up. Going to package this VM and upload to people.mozilla.org to update the starter box. That should get us over some humps in general