And under the old system, if your upgrade did not clear in advance, you could not even request one until 24-hours before your final AC segment when doing online check-in if you had a multi-segment journey. This meant there was no way to request an upgrade until well after everyone just flying the initial segment had done so. Now we don't have to worry about this situation any more, since our priority on the day of flight will be based on when we made our original request, not when we were able to check in.

New system much fairer
 

for the reasons discussed above.
but I am wondering about this:

"If you're travelling on a direct flight (i.e. a flight operated under a single flight number but with a stop en route), you can only request an upgrade for your entire itinerary."

Examples would be YYZ-YVR-SYD (or YYZ-YVR-HKG) Does this mean that that the entire flight (both segments) can be upgarded at the 168hr, (or 96 hr) mark from the first airport (YYZ), or would it be from the stop (YVR)?

Should be from the first airport. I haven't had the opportunity to test it.

I agree it should be from the first airport if you book the Direct flight, but if you book as two segments (YYZ-YVR then YVR-SYD) - which is possible and a different scenario - it would be two separate requests eligible at different times.

Let's say you're booked YYZ-YVR-SYD and for some reason they are booked as separate segments.

Suppose you call at the 96-hour mark with respect to the first flight to upgrade YYZ-YVR and lock that in.

Then suppose you call at the 96-hour mark with respect to the second flight and find out you can't upgrade YVR-SYD.

If you then opt to downgrade because upgrading YYZ-YVR is worthwhile to you only if it's part of the full YYZ-YVR-SYD journey (after all, it costs you the same number of eUpgrade points regardless of whether the YYZ-YVR segment is upgraded), would you be charged the fare difference to downgrade YYZ-YVR back to economy?

If so, that's a serious fly in the ointment.

There's been discussion about that scenario in another thread and it does appear that there's a fly in the ointment. I think you should be allowed to cancel the upgrade as long as the economy cabin isn't full, but that's not how it works currently.

OLCI changed as well
 

I just tried to check in for my upgraded flight. The same issue pops up for me. I have to wait to T-24 hr before my LAST flight. I wonder if the same software (new software) is running EUpgrades as well as OLCI?