My approach to such contests in advising 30 yearbooks was to simply think of contests as one more thing to schedule. It took me some time to figure this out, but eventually, I kept a folder in which I would save copies of what I considered my students' best work as the year progressed. When March or April came along I did not have to browse through the entire book's PDFs (and I did the same with newspaper), but already had sifted through much of the material.
It takes very little time these days to log on to contest sites and upload PDFs and enter a few other pieces of information. The time-consuming part is having to switch gears and sort through student work, all while trying to wrap up the book or prepare that final unit or get a daughter to her soccer practice.
I learned later that what I was doing was essentially conducting a formative assessment (rather than the traditional summative assessment after publication that yearbooks usually entail). If I found that I was not seeing much quality arising out of the first deadline or so, that helped me focus my teaching on helping students "up their game" a bit. This probably sounds quite elementary to you, and it does to me as I write it. But I valued the excitement and pride of being able to share awards with students at the end of the year so much that I never regretted those few hours spent along the way collecting good work. Most years I even gave my own informal awards for best writing in Deadline 2, or best spread from Deadline 3. Those in-class ceremonies were a good excuse for cake.
For much of my advising career, we had to literally cut up books to enter in contests. At one point I was ordering 6 extra books that would eventually be cut apart with Xacto knives and attached to paper entry forms. So much for the "good ol' days." PDFs are so much easier.
Some advisers believe strongly in students having the responsibility for all contests, but I never had students choose entries. I did it based on my experience, trying to consider our work from a stranger's perspective. I have been a judge for a very long time and I know what judges tend to look for and reward. This is one reason I urge advisers to consider judging and never to think they "just don't have the experience." Judging can be an adviser's most important professional practice.
I provided plenty of "go out of my way to praise" support for students who needed it, usually in long conversations, but I never entered a student's work to make that student feel good. I never told a student I had entered her in a contest. I only announced winners, so I never had to spend much time commiserating with students about why they did NOT win. I got to spend my time on celebrating. I was always clear with students that awards are a bonus, and often wildly inconsistent from judge to judge.
Yearbook is such a thankless job, for the adviser and the students. The school community will never comprehend how much work even a mediocre book is. And a terrific book is just taken in stride. After all, your readers don't normally read other schools' yearbooks so they can't compare. All those award certificates can and should become part of the conversation you might have with your principal about your program and maybe about your teaching assignment.
Critiques have the same purpose: to confirm the adviser and staff's feelings about the effectiveness of their work all year. As with athletic success, publication awards can add to a school's culture.
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