I am an experienced
DVC member and experienced walker. In the past, I received a different error message saying that the villa was not available when that happened. Not a "technical difficulty" message or the dwarves.
I'm not following what you're saying about check-outs. If someone checked out on 4/25, then their villa would have been available yesterday for check-in. Secondly, 4/25 became available at today 8:00:02 (I had time.gov up for a countdown). There is NO WAY that a human could modify their reservation at 8:00 am and finish 2 seconds later.