I’ve definitely tried to trace out circles in Shmeppy to little avail… This seems like a good idea, though it’s not super clear to me how I’d implement this. All the modifier keys are being used already (Ctrl can’t be used unfortunately, Firefox has special Ctrl+Click behavior that can’t be disabled by a website), but even if I could use another modifier it seems like I’m starting to push how much functionality I can dump onto the fill tool via modifer keys without becoming kinda overwhelming.
Interestingly, essentially the same problem is cropping up in Feature Request: Spell AOEs. There’s some additional shapes I want to support, but there’s no clear way to do this that feels like it doesn’t seriously compromise on ease-of-use.