I'll start off with some encouragement. It's good that you're asking for advice as to how to improve your look. It looks pretty good, although as with anything, there can be improvement. Good job so far! What, in my opinion, would be great help, would be to improve the length of the hair. It hasn't been mentioned yet, but I think the best thing to do would actually be to grow it long again. From experience, men prefer long hair. It's work to maintain it, to wash it, to dry it, but it pays off. For example, I know of a woman that had long hair, and looked great with it. She ended up getting a new hairstyle, and it was shorter than yours in your last pictures. She dropped about 2, and perhaps even, 3 points on the scale of attractiveness. To add insult to injury, she had also gotten married and almost immediately she got the hair style change, which shows a nasty side of her personality: she doesn't care what her husband thinks about it, she just landed her husband and then stopped the act. To be fair, she may have problems. Nonetheless, she lost points on the scale, meaning she wasn't that attractive anymore. I'm kind of worried for her actually.

Taken right now. Short hair grown out. I need another change. This time I'm thinking chin-length with a lot of layers. But I want something bright and colorful to match the person I am now. Bright orange is a possibility, as is a dark auburn. Help me decide! I would greatly appreciate any thoughts!

In my opinion, grow it long again, as in the first picture. Stay with the natural color of your hair, dying hair to bright colors is immature and has a bad reputation of that as well as mental illness. If you get it long again, and allow your hair's natural color to continue to shine, it would both increase your attractiveness and would be the best option.