Welcome Ben Lipsey. (And welcome back Ben Smith.)
It's nice to see you here. The sudden burst of transparency is most refreshing.
For what it's worth, some unsolicited advice -- please pace yourselves. I don't think anyone wants you to OD/burn out on FT quickly. (Perhaps the moderators could set up a Q&A forum, wiki, or whatever else they have... where an "Ask an Exec" program might be set up.)
Two observations... both of which have been alluded to earlier.
The first is if you are going to cut back some service and benefit, just come out and state it directly. Justify it if you have to, but be direct. I'm certain a great deal of anger has been unnecessarily generated because of the perceived insult of many "enhancements." I'm equally sure that if it was addressed directly, people would still be unhappy or disappointed in the cutback, but at least they wouldn't be insulted. As well, the issue would likely fade much more quickly. (Likewise, don't announce a bunch of major cutbacks then focus on a single meager improvement.)
Secondly, it seems to be a continuous refrain from Air Canada that because of some minor perceived problem with a potential solution, the solution needs to be abandoned completely. Often it sounds more like "it's tooooooooo haaaaaaarrrrrrddddd..." Other times it just seems like an excuse to not do something. (The decade long campaign for lifetime status comes to mind.)
There are two examples within this very thread - using alleged privacy concerns to justify not making upgrade lists publicly available, and the perceived threat of "irrational" travellers to apparently justify not doing, well, not doing lots of things I suppose.
As someone else noted, the privacy concerns can easily be overcome in lots of ways - using initials, using 3+1 naming like the American carriers do, using the last few digits of the Aeroplan number, using the last few digits of the ticket number (as printed on the boarding pass), and so on. I'm sure there are more ways yet.
As for the irrational, they will continue to be irrational no matter what. On the other hand, the normally rational can be driven over the edge by a lot of absurd things airlines do. If you are concerned that someone will complain that they were #6 on the upgrade list and now they are #7, then you simply need to make it clear before they can access the list that the list is not guaranteed and always subject to change. For good measure, you might include a few examples as to why.
This fear of... damn near everything... but mostly the fear of not being perfect leads to paralysis. It's been the subject of cultural fables for millennia. We've all seen that too many times.
(BTW, if you think you have a problem why not, as often previously suggested by many, turn it over to the brain trust here. There is a huge conglomerate of creative, original thinking here -- as oft demonstrated by the way FTers take maximum advantage of FF programs and airlines.)