You can use checkboxes to pick what work needs to happen for an item. But they are time-delayed (it doesn't change the current checkbox checked value until the next time you make a change). I couldn't find a fix for this. Checking in so that I can try another route (using objects instead of key strings).
Now using objects for the help kinds checkboxes. No change. This is just a bug I can't / won't fix. Probably OK, since I will be the only one using it. Moving on.