I feel this in my bones. You're pretty much a mini me. I'm a master of many things and a jack of none too. I threw my Rubik's cube in the closet the day I got it because I couldn't solve the fucking thing on the first try. If it doesn't come easy, I'm out.
Being forced as a child to do something just because you're good at it is something that still sticks with me and that I will rail against forever! I worked very hard to NOT do that to my boys, and it was way harder than I thought it would be. Sometimes, I slipped. My parents used to use religion to justify that bullshit. God gave me whatever talent was at issue and it would be a sin to waste it. I had a responsibility to make good use of what "he" gave me.
Regarding the writing, also same, hid it for ages. Here's the difference for me, now that I'm out as a writer, it's a talent I have that I'm choosing to pursue. I'm in control of this accident of genetics that allows me to put words together. I have tons of fear and still get in my own way all the time, but I'm aware of it and I can choose to do something about it, or not. Obviously you're aware of it too.
Regarding contests, if you're talking about Vocal, fuck 'em. I've won and placed several times in their contests, as you know. And I've lost plenty. They have obvious favourites and flavours of the week. I was one for a short time. They also favour new writers over writers that have been around and paying their fees for a while. No wonder, when your stock is literally circling the drain, you want new money coming in. Contests are only as good as the people judging them, remember that. You are a good writer, I know because I don't read bad writers.