Thanks so much for the reply!
When are you looking to travel?
We'd like to get there somewhere between March 5-7, 2019 and leave around April 16-18, 2019. March 7 - Apr 16 is probably ideal, and the date I checked upgrade availability on (for returning anyway).
I was planning on booking within the next couple weeks and get it out of the way, but I'm not sure I'll have the UR until Nov. I therefore figured I'd start the upgrade process around Nov-Dec, so any hold would only need to be as long as it takes for the UR to transfer, but looking through the KE website and other threads here, I haven't been able to determine whether the upgrade process needs to start within a specific timeframe or can be initiated whenever.
In order to upgrade your girlfriend you would need to add her as an authorized user on your Chase card and then transfer points to her UR account. She can then transfer them to her own skypass account. You can not upgrade her from your Skypass account as you are not family.
If you skim any recent posts on this forum you'll see that there have been changes to the Skypes program, most notably that UR transfers are taking much longer than they used to and that KE is no longer holding reservations (which was ridiculously generous anyway IMO). Also, some people have noted that KE of not releasing as many award seats as they used to. Hopefully not allowing holds will help with the inventory issues.
Yeah, the AU stuff is no problem, although I did see the posts about UR taking forever. I'm basically assuming as a baseline we'll each have the 50k ready to go. I was just concerned about whether she could even upgrade her portion of a 2-person ticket booked under my account, since all of the upgrade stories I've seen either involved spouses/family or single travelers.
Personally I wouldn't redeem points to upgrade as M fares are expensive (for having to sit on economy) and upgrades are not a great redemption value since a one way J award is 75k points and an upgrade is 50k, but I understand that it may be worth it for you!
I know it's kind of an awful deal, and it doesn't really look like M class gets us anything else (change fees seem identical, etc). It would also really suck to pay all that money for M class and then be unlucky enough to watch all the upgrades disappear. If this plan ends up being too infeasible, we'll throw in the towel and save the points (maybe try to get a paid upgrade at the gate?), but I'm concerned enough that I really would like to make it work if it's not too logistically nightmarish.