So I thought I had solved my problem with Shoelace by taking out a small but apparently key bit several scenes back. Only it turns out I didn't because there's a major logical flaw I missed while I was plotting this out and by rights the protagonist's semievil semiplot should be ending right here. Dammit. Now I don't know what to do. Maybe I can recruit the real villain to help me out.
In the meantime, I have been critiquing my brother's first writing assignment. Several weeks ago, he said, "I feel like my writing skills are getting worse. So I was wondering if maybe you could give me some assignments and help me out so I could practice." I found this utterly charming and assigned him three paragraphs on the history of ice cream. He sent me his three paragraphs a couple of days ago and it's evident that he needs some instruction along with practice. His grammar and sentence structure are fairly decent, but I get the feeling that he never quite got the idea that writing is used primarily for communication. I admit I did not explicitly say "This is a strictly informative, semi-formal essay" but it's my belief I shouldn't have had to. His essay is nonlinear, overly informal and joking, and isn't focusing on communicating information, even though that's what I asked him to do. I'm not sure what its focus is. I don't think he does either.
So I'm sending it back with a bunch of comments (and a couple of corrected commas and semicolons, but there are no misplaced apostrophes so I'm pleased there) and suggestions on how to improve it with reasons why they would improve it, and I'm going to ask him to revise it. After that, I have plans for more assignments to work on informative writing, persuasive writing, and descriptive writing, using examples he might actually use--memos to employees, cover letters, advertising copy, a letter to his daughter, and so on. I hope he's willing to stick with me enough to get through this. I think he could do really well at writing--I was talking to Mom about this and apparently she and a lot of her family have always been good at it; why didn't I know that before?--but he needs some guidance to get there.
I'm also bemused to find that while I still don't think I'd be a good teacher, I'm enjoying planning out lessons as a tutor. Luckily it's not fiction we're talking about, though, since I don't exactly feel qualified to teach about that these days.