Here’s my conclusion: It was a bad idea to ask for input. I really appreciate everyone’s comments, but asking the Internet for input on a personal representation of myself doesn’t really work. It's like saying "Do I look fat in this?" I’ll mark it up to an experiment.
In college I was buying my first suit and completely perplexed about what kind of suit I needed. Dark/light? 3 buttons/2 buttons? Cotton/wool? A girlfriend at the time gave me some input I’ll never forget. She said: “Lee, you pick the suit that makes you feel confident and powerful. Nothing about the color or fabric matters- it’s how it makes you feel when you wear it that matters.�?
Applied to the buddy icon thing, the advice is still true for me. Good lighting, closed mouth, looking into the camera- I know these are the hallmark of a good portrait. But is it how I want to represent myself? Only I know that.
The fact that you took the time to provide your input means the world to me, really. I just hope you won’t be upset if I don’t listen. Personally, I'm not a fan of picture #2 at all, but that’s just me. I’ll figure it out eventually.