I have been able to do this in the past without issues. Out of curiosity what is the reload time on your buoy launcher? If you use 30% size with a large buoy and low reload tech it might not finish reloading before reaching the POI.
This was a great suggestion and point, and an aspect I did not initially test. I was originally using 30% launchers in my game. So I created a scenario where I had both a "fast" launcher with a 45 sec reload, and a slow launcher, with a 3600 second reload
Both exhibited the same behavior, even when point to point transfer was hours > than the reload speed.
Example test: "Fast" [45 sec] reload buoy ship, Launch Ready Ordnance order at Sol Comet Wolf-Harrington [Current location] -> Temp Waypoint in between -> Enke - travel time required 11.3 hours total. Waypoint is roughly halfway between. Skip 1-day increment results in a 11:30 timeskip, Wolf-Harrington has a buoy, the temp waypoint is gone with no buoy, and the ship is awaiting new orders at a buoyless Enke. Only the first buoy drops.
tldr; I can replicate this issue with a brand new aurora install, with a 45-sec reload launcher that should be ready during that time frame.