Thank you for your feedback, I will pass along your suggestion (#1) to my engineering team. It sounds like your audio setup is a bit different than that of our typical user, however we will look into what can be done for this kind of multi-output setup.
As far as problem #2, we have a setting for “Plug-in behavior” that you can set for when you plug in an aux jack to your computer. It can be set to “Ask”, “Change to Headphone listening”, Change to Desktop listening”, or “Ignore.” It’s default is set to “Ask”, so I’m not sure why you weren’t prompted to make a choice when you plugged in your headphone jack. This too might have something to do with your multi-output setup.