I sometimes work with a proofreader (though not on this SteepandCheap email, as I'm sure you realize). Corresponding with her one-on-one via email is very stressful for me. I don't think twice about the content I'm sending in an attachment for her to read, but I'll agonize over the grammar of the emails I send. And when she replies, I comb through her emails with undue patience looking for grammatical errors. I always find them, or at least I think I find them. I suppose the reason I need to work with a proofreader is because I'm not certain whether the errors I'm finding are actual errors or things I'm imagining.