is there a point where I will be so comfortable as to not need to fear misspelling something without this crutch of autocorrect?

I can't speak for how long it will take you specifically, but yeah, I absolutely think you can get to that point. I don't really remember how long it took me to learn, but it couldn't have been more than a few weeks, and I think I had some factors which were working to my advantage, anyways. Have you adjusted any of the settings?