Heya guys. This is totally not official so don't take it as fact. It's just from my experience in both entering and/or following dA contest trends over the years. I'd love to hear other opinions and input.
1. This is the most important. Be an AMAZING artist. I can't stress this enough. dA and its affiliated judges do not pick mediocre art to win. It always throws me when people complain that amateur artists never win. the stakes are usually pretty high. Of course only the best are going to win. They don't become the best over night. It takes years of practice, blood, sweat and tears.
2. When given a theme, your chances are greater if you follow it in a more literal way. Sorry guys, metaphors or outside of the box thinking generally doesn't make the cut. It may get you in the semi-finalists but that's it.
3. If the theme gives you an option between personal experience and portraying what ever is being promoted, go with option two! These contests are fun but keep in mind, they are also marketing tools. There will be the occasional token entries that make the semi-finals without using the theme X, but they never actually win.
4. dA makes mistakes. Sometimes they pick people who broke the rules. Personally I think this needs to be addressed in a better way than letting it slide, but that's just my opinion. Lesson learned, don't take official rules at face value.
5. Popularity means nothing. People have been accused of winning because they are popular but this is totally not true. I've seen some of dA's most famous artists not even make semi-finals for reason x or y, I don't really know.
6. Judges are people too, their tastes are likely not going to conform to your tastes. Some contests disclose their judges. Some don't. It's easier to get an idea of what people are expecting when you know who's judging, but if you keep an idea of the general choices made by staff here over the years, it may give you an idea of what they expect. At the end of the day I've been both surprised and not surprised by semi-finalists, but have been typically able to predict the winners based on past trends.
7. This isn't really a way to win, just a fact. Digital art usually wins. People say that traditional mediums never win because of the judges but here's the likely reason. In dA, the pool of digital art entries is vastly greater than that of traditional art. Digital art is just more popular here now. It doesn't mean that traditional art is dead. It's just that digital is the majority HERE. There are traditional art only contests out there with stakes that are just as, if not higher than the contests here on dA. Don't forget that traditional folks.
8. Just because these trends exist now doesn't mean they won't ever change, and just because your entry follows all of these, does not mean it will win. At the end of the day, you never know for sure who will get chosen.
That's all I can think of for now. Might add more later. Hope this helps.
Listening to: Nothing
Watching: a wolf documentary
Playing: Flight Rising