I miss summer, too! I don't know if it got as cold in Portland as it did here last weekend but everything now that it's thawed out has that dead and beaten up look to it.
Yes, I do get a measure of satisfaction from knowing that my writing is pretty good. It's not really about impressing anybody else, it's just about knowing that I've done a good job, for its own sake.
From where I'm sitting, I don't see any significant harm and looping as long as each iteration brings you closer to some sort of resolution. The problem only arises when you are truly stuck in a rut repeating the same thing over and over and over without life feeling any better.