Yeah I hadn't been able to figure this out.
In the 2016-17 database, the settings are (Round, Actual Dates, "Draw Date" and Year Offset in Schedule)
Pre-Q: Nov 8-11 (M-Th), 1.9.2016, Offset 0
Final-Q: Feb 6-9 (M-Th), 1.12.2016, Offset 1
Oly: Feb 14-25 (W-Su), 1.12.2017, Offset 1
I don't quite get how the schedule offset and the draw date affect things. I know for certain that in my 17-18 DB, the Olympics stop midway through the finals/playoff. I also know that for certain this is because the NHL Alternate Schedule Template and the Olympic Scheduling are not playing nice together. The dates look fine in the editor in terms of the Alternate schedule having an appropriate break but then, because the Olympics have a "day of the week" attached, it slides the Olympic dates around, causing a clash and causing the Olympics to simply stop midway (and likely guys not returning).
For example, it my 2022 season now, the Pre-Qualifying and Finals Qualifying all went off without a hitch. The Olympics started without a hitch, Group Stages went fine but then the Olympics "stopped" after the Playoff Quarterfinals. And I know why - the Olympics are flagged not to interfere with competing competitions - of which I assume the NHL Alternate Schedule is one.
So even though my Editor says the Olympics are to start on February 14 (Wednesday) and end on the 25th (Sunday) and the NHL alternate schedule has a break from February 9 through 25 - the actual start date of the Olympics is February 16 (Wednesday) and end on the 27th (Sunday) and the actual NHL alternate schedule has a break from February 7 through 22. So when the NHL resumes on the 23rd, the Olympics freeze up and although the game keeps playing, no Olympic history is recorded and the NHL players don't come back from the twilight zone.
But neither the Olympic Schedule nor the NHL alternate schedule match up in the editor with real dates. I get why the Olympic schedules shifts to the nearest Wednesday...but why does February 9 in the NHL schedule template not equal February 9 in the game?