Amanda: I'm a big fan of the "pretend you only have one tag" technique. Yeah, it doesn't work often in real life, but it's a great way to hone one's thinking.
Make every tag count. Make sure EACH TAG leads directly to your item.
I have to confess that I've been taking the cleanse at my own pace and have put a lot of the tag/title days on hold because I know they're more time consuming. I am still committed to getting them done! I'm finding it easier to go by shop section and have gotten two shop sections done so far.
I had a long day outside of Etsy. Only got 3 items done. But, I got them done. Will work on a few more before bed (I'm a night owl/nocturnal). It takes me a while since I'm looking up keywords on Google first and then starting over completely on some listings. So I'm going slow, but I'm still going.
My strategy is to begin at the end so I don't get confused with new listings. That, and those are the ones up for renewal, so they get refreshed with new keywords when the time comes.