I've entered a pretty large number of them and I haven't really felt all that bad about not winning any of the nth post or RNG ones. The first I won was from a design contest and the second was a win for everybody on the eve of the new year.
Honestly I don't think it's preference towards anybody in particular, and if there were in any sort of way, there'd be other, better devices to do so (like mentioning someone specifically or contacting someone in particular telling them that they won or have a special privilege). As we know, specific people have been rewarded for their long-timer status and support of his work.
As discouraging as it is to lose, the best we can do is have as much fun as cc does (because it's quite apparent to me that he does love us, albeit in strange ways at times). Think of it as if you were in his shoes, wouldn't you like that your fans and supporters were just enjoying themselves and your own work? If you like what he does overall, the best is to remain supportive and positive, especially when it's already so hard to maintain this operation going. Remind ourselves that this hadn't happened for quite a long time, and he has even given the chance to entries from over 2 years ago (see radnelac ii).
Ultimately, I am happy that I have gotten the chance to support his work directly and that he is back with this community even if it's a short while (it has already been much longer than I expected).
