calgal said:
Pat, can you waitlist for a day that is more than 331 days out? And will you reliably get priority over people who call at 1AM on the day the seats load if you do that? Yesterday I called UA to put outbounds on hold at a fee of $15/ ticket for calling in instead of using united.com. My plan was to call back the night the inbounds loaded to get my return FF reservations. Alternatively, could I have booked online for example outbound 3/31, return 4/1 and just waitlisted for the return I really wanted?
(By the way, my return date was 4/8 and, while availability online was 4/6 or sooner, the CSR was able to book my returns on 4/8. I was very surprised and thought it must be an advantage that they offer to encourage people to call in and pay the supplemental $15).
Regarding UA, I'll share my experience...
I have never attempted to waitlist for dates beyond the 331 day reservation period. I do not think it is possible, but it never hurts to ask. IIRC, UA has shortened their hold period to 48-72 hours, I don't remember which.
Elite status helps, not so much with priority (unless 1K or UGS), but with getting better reservationists. This is critical with international awards and even hard to get domestic awards like Hawaii. If things don't feel right, end the call and try again.
I rarely attempt to make reservations at the outer window, rather I just find (on the phone or web site (phone for international)) availability and book what I can, if my desired dates aren't available. So, if I was wanting to travel next May (not available yet), I'd just find something in April, book it and waitlist for the May dates as they became available. Also, if I desired a different booking class (like XC or XF (Business or First)), I'd pay the extra miles and waitlist for that too. Also, IME, it's easier booking tickets as singles (different PNR's) and then linking the PNR's later, since UA/*A will often only release one seat at a time (especially XC/XF).
Since my wife and I don't mind traveling at the last minute, we just wait and see and often end up somewhere we never thought we would. I find lodging (even timeshares) much more flexible than airline award tickets so I just follow the path of least resistence
Lastly, I always plan a few days on either side of a planned vacation stay, to allow for flexibility when negotiating for our desired award dates. The important thing is to have something, because only the airline knows how many people are interested in what you have

Or so I was told

I would watch our PNR's online as my wife's client would manipulate them over the period of months between booking and travel and it was just amazing to see the things she did. I was sorry to see her retire, but UA shed a lot of good people during BK.
DaveM, for one, has extensive experience with UA, so I imagine he has a lot to share with you. Good luck!
Pat