The drop-off HUGEHandyman is describing is almost always a framing issue, not an AI issue. When the first thing someone hears is "I'm an AI," they're being asked to make a decision before they've gotten any value. Most people opt out.
The setups that actually retain callers lead with the task, not the identity. Something like "Thanks for calling, I can get you taken care of, what's the address for the service?" gets people talking before they've decided whether they care what's answering.
For your specific situation, the relationship concern is valid but the missed call problem is real too. The middle ground a lot of family businesses use is letting the AI handle after-hours and overflow only, with a clear handoff path to you for anything that needs a real conversation. That way you're not replacing the connection, you're just not losing leads at 9pm.
The rescheduling on unavailable days issue roselvaggio mentioned is a real gap worth flagging to Jobber directly. That's a calendar sync configuration problem and it should be fixable.
