I like the jacket on you. It's got the mixed media and moto thing going. This is a cute casual outfit, the jacket definitely brightens the look. Have you tried it with a simple white scoop neck tank top? How about wearing it closed like a blouse with cami underneath? The boxy, closed jacket look is on trend right now.
With my orphans I either re-offer them at a lower price (I too am listing on eBay right now, cleaning out my closet -- I have the time!). Or, I donate them. I've only a few times changed my mind about taking something out of the purge pile. I tend not to beat on myself too much for mistakes. I still make a lot of mistakes, it's constantly a learning process. And when I have to take the time to sell my mistakes on eBay (most of them barely worn or even NWT), it reinforces the learning.
I have noticed that I have made fewer footwear mistakes/orphans than clothing mistakes. That is because I am quite picky about shoes, I know what I like, what I don't. Whereas I tend to like more clothing. I see potential in so many pieces on the rack, whereas that isn't the case with shoes.
One thing I am trying to do now is to shop outfits more than separates. Sure I have my jeans/tee/cardi formula for lounging at home which is all about separates, and they don't always need to be chic together. But for other wardrobe needs, I am trying to purchase around a complete look now.