I read your post and I understand it (meaning I feel empathy for some of it).
However, wanting an award so badly ain't the right motivation, and it shouldn't be part of who you are.
You should be proud of everything you create, whether you win prizes with it or not.
Mass rep and awards are ego boosters, and I didn't think you'd need them.
Creating those immense hopes of having a good chance of winning will only increase disappointment when one doesn't. Don't put yourself through that kind of trouble.
Just look at where you are now. You have made quite the evolution, and you are improving still. THAT is the award you should wear proudly.