Nope it doesn't!
Multiple people have reported that it completely depends on whether Apple Gods become happy with that step. Sometimes its a combination of steps (i.e. delete and re-create the Apple-ids, reboot bot machines, re-start finders, etc.). By far the most consistent way to get it to work is to reboot both machines which may allow you to do ONE transfer (the next transfer fails).
BTW, just so you guys know, there are apparently multiple active threads regarding this issue. Tells me that there is a deeper problem (very un-characteristics of Apple since most of the time whatever they release, it just works)