It feels like this is the intent in the way Hubspot is designed but it just doesn’t quite get there. Definitely keen for this.
There is a workaround using an if/then I think, and just doing it all in one chatflow. From memory, set up a chatbot and then have an if/then to assign the chat to a livechat with someone on the team if they are marked as available. Unfortunately that doesn’t work for us with our particular subscription type.