I had the same experience in the contest you are referring to.I kept submitting name after name they said they liked, and sent me private messages about,saying I was totally on the right track, spot on,they love it, etc..and I got good ratings on them. I thought I had a great chance to win, and was trending.Then all of that was for naught.
I think we all experience that.
I think it's just more depressing and frustrating at times, as just in the few months I have been here, I can see cycles and trends in what names go over well,and at least for me...I am just not really finding a niche for my names lately.
I also know as creatives we probably have a certain wheelhouse and contest fit for our kind of names, especially if you are a person who takes this seriously and works hard to come up with what you think are appropriate and relevant names,and not just submitting hit and run names.So sometimes they are the "names du jour" and other times not so much.
So even though I have been discouraged about alot of things here lately..I still try to hang in, hoping the tide will turn my way again.
So hang in! If you have confidence you can name well, than it is worth pursuing.
Not winning, often has little to do with the quality of your name if you are a proven namer..but rather more with the way the tides are at the moment.