As in the music analogy, you need a huge amount of input time to get to a good level of proficiency, I seem to recall, from past forum threads, IIRC, with people like
@custard and others, discussing this as a number, gets into + 10,000 hours, and that is with tutelage.
My plan as I approach retirement is to up my game, with the scaling down of my joinery activities, to go on to make smaller items such as "jewellery boxes", which I've no doubt will be a complete waste of time, for several reasons, I've never made or sold anything speculatively, and that there are far greater skilled people than I already in that market, so i may just end making rabbit hutches and bird boxes, nice ones though.
and a drum sander at some point
On my list at this time as well, been putting it off for years, I have some quite complex curved lamination projects in my back catalogue to make, that I
WILL need one for, (looking at the Laguna)
Start with cheaper construction grade timber and just start
I'm not an advocate of that idea, using poor quality materials will lead to frustration and a rapid loss of interest.
And whilst not deriding Men's sheds, they do have people with diverse skills and capabilities, but in my experience,"fine" woodworking isn't really one of them, and I include myself in that.
Further to the "mentoring" part, I have been doing some this week, with a retired lady/widow, who has the desire (read defiance) to be self reliant, but got into a bit of a muddle.
She had bought herself some basic hand tools, hand saw, drivers, hammer etc and mixed boxes of screws and nails, to do some work to an old shed's panels (P.A.T), I had some excess shiplap cladding left over from a job a couple of year's ago, and between all of us, she has more than exceeded her expectations, the pleasure I derive from helping is simply the big Thank you at the end, consequently her determination, now, is to do even more, with the confidence that she derived from the experience (with a little future help and guidance, I might add)