Originally Posted by
laginibre
1/ Should I waitlist both of us now on one of the legs and hope that we both clear together (I'm Plat; she's General Member)? What if I'm the only one who clears? Can I decline the upgrade? Of course, if I do that, there is the risk that my exit row seat next to her might be gone...
2/ Should I wait until, say, 100 hours before departure and see if RPU upgrades are available for both of us at that point?
3/ Should I just check us in (making sure we're together in Economy) and wait until we get to the airport to see if we can both be upgraded on my RPUs?
This is now a real challenge if you book on separate PNRs.
Your best shot of both getting upgraded comes if you both waitlist now. But there is a very real risk you will wind up flying in separate cabins. If you do this, continue to check frequently for R and call it in if you see open R.
Chances of both clearing using either other approach is lower. No. 3 is particularly unlikely to work.
The other thing to do is try to SDC into open R at T-24. Unfortunately, UA is much less likely to open R at the 24 hour window than it used to.