I think your hair is lovely, but I can see that it's short enough that it would be a love/hate thing. When I cut mine, I love love loved it for about four months and kept it at that length, and then overnight I was DONE with short hair. But unfortunately being "done" with short takes more patience to fix than being "done" with long.
As I'm in the midst of the re-growing-out process, it does indeed seem like it takes forever. FOREVER. It's been six months and I can feel the difference in terms of being able to put it up and stuff, but it seems like it looks more or less the same.
Trimming: First of all, I cut my own hair, because I live in a very rural area and don't have access to hairdressers who won't butcher it. Last time I grew it out, I trimmed fairly regularly to shape and long-layer it in addition to keeping the ends healthy. This time around, I've been keeping an eye on the ends and moisturizing the heck out of them - I put cocoa butter on them every other day or so, which they love. But the trimming I've done has been on a curl-by-curl basis, in small amounts, to fight split ends. It's not a particularly scientific method, I just trim when they feel like they need it.