The transition I'm making is going from "one day" thinking to "happening then" thinking of that makes sense?
Yes, that does make sense. Particularly given how young you both are.
You've lots of time to plan and get everything lined up.
Music is a tough field for sure. Is that also the hobby?
It'seems a good one though, because it should enrich your life for having done it even if you never work in it.
If music is the hobby that sometimes pays, maybe a way forward would be to stop all the work applying for jobs for a while. It is such an exhausting and demoralising way to spend your time and then concentrate on the hobby/job.
I know the restaurant work is enjoyable, but does it clash with music playing opportunities? Which would he drop if he had to choose?
There are so many choices to be made and opportunities to be taken for a 27 year old in his position.
Those things close down when you have kids. For a while anyway.
Just don't close them down too soon out of fear.