> I want to reduce the chance of them getting frustrated with the app and silently canceling the subscription. I would rather they reach out to me, so I can fix the problem or fill the gap they're facing with the app.

I think when people have a technical issue they're more comfortable with an 'open a ticket' pattern rather than an 'email $anon' pattern.

I think you should spin up a Trello or a Jira or something and send them an invite to an Issues board.

Where I currently work, Desktop Support is a dude named Justin. When I want something I open a ticket in the Desktop Support portal. It would feel intrusive if I had a problem so I just called Justin up.