Because updates wipe observer mode clean, the ideal timing for an update to go live is right before (within an hour or so) either the european or american daily AT starts, when the previous matches have had time to be watched and are likely to be pushed off anyway. This is mainly in comparison to observer wipes that happen during or immediately after an AT.
I get that pragmatically the subset of people interested in observer mode is small enough for this not to be a huge priority, especially when updates are done more rarely. But in the last few months the live team seems far more comfortable putting through mini-updates constantly, and there don't seem to be many other relevant concerns for the timing of updates during a day. At most the update timing would be pushed up or delayed by a few hours to avoid this oversight, so I suspect it's just an awareness issue that hopefully the CR team can pass along.
