I've been meaning to automate some repetitive stuff like this too, but I always forget half the AppleScript syntax by the time I need it again. Love that you stuck with Claude through 10 iterations—sounds like the back-and-forth actually mirrors your usual debugging process anyway, just faster. The clipboard trick is smart, definitely stealing that workflow. By the way, I'm working on Inkfox AI, a free unlimited AI image generator with no signup required—if you ever need quick visuals for those system reports or anything else, feel free to try it out.