Thanks for sharing the story, Per!
Have you pondered selling credits? So it’s not like paying $10/chat individually and making a decision for every wuestion.
Make a deal with getting a few chat credits up front for a discount where each credit is worth 20mins or 30mins. My hope’d be that this reduces the friction: once you have 5 credits or so for $40, you’re more likely to come back for help when the first experience was good.