The broader issue here is that my players shut down if their first approach doesn't yield fruit. I am really trying to break them of this habit and teach them that it is ok to try different things.
This sounds to me like you are trying to train disobedient puppies. That you are effectively trying to rub their noses in their messes so they don't do that again.
Created an interactive character sheet for sidekicks on Google Sheets - automatic calculations, drop down menus for sidekick type, hopefully everything necessary to run a sidekick: https://tinyurl.com/y6rnyuyc