Ehh, I think it's just both organizations pointing the finger at the other and neither wanting to hold itself to a tight standard knowing that the other could be the holdup.

I've never had experience transferring Hilton -> airline, but I've done the opposite several times and they never take as long as I'm warned they might. For example, I just did a transfer from VS to Hilton and, despite being warned it could take a month, the transfer completed in 3 days.