Mike Rowe is always on this topic, but I have had two experiences lately related to this.
First, I have a clock repair shop that I use. Clocks, not watches. He told me that his current repair wait line is 2 years. His expertise and pleasure is antique (over 100) clocks, including grandfather clocks. He'd be glad to get two reliable and interested apprentices, but can't find them. His last one, who he felt had talent, stole from him so that was that.
(Tips for old clocks: Never overwind. Never move with pendulum attached. Only correct time forward, with minute hand only. And be aware: some old clocks rewind clockwise, some backwards)
Second, my firearm expert recently died. He had a firearm woodworker with him. I counted on their skill for all of my firearm glitches. He had tried for 5 years to recruit apprentices from the local high school with no response. He was plenty busy but wanted somebody to take his business over. It is gone.