I can be picky about language. But I'm also usually ready, before most of my bookish friends, to throw in the towel when a certain "incorrect" usage becomes common.
Like the disappearance of the word "whom," or like "they" and "their" as genderless singular pronouns, since "zhe" and "herm" never really caught on. I'm slowly getting used to that. I don't like the role of pursed-lipped school marm, but I do appreciate precision in written and spoken language, so it can be a hard call. When do you give up?
I think I see "loose" used for "lose" more and more often. In fact, I think I see this more often than I actually see the word "lose" written. And now I'm starting to notice that people use "lead" instead of "led." These are both spelling rather than syntax issues, and I tend to be even less resistant to spelling irregularities. Sometimes I even like them. I like "thru" and "tho." I like "tonite." English could certainly stand some housecleaning in the spelling department. Lose/loose and led/lead types of problems are inevitable when your language has more exceptions than rules. Still, it's jarring, because in my head, "Did you lose your sweater?" is very different from "Did you loose your sweater?"