I've had to teach a lot of young men how to hand file over the years.
Now some can pick it relatively easy and some can't no matter what, it might be something to do with hands not connected to the brain.
I've also had the opportunity to see/view a lot of professional cutters hand file sharpen their saws.
Now again some are good a natural at it and some are pathetic at it no matter how many years they have been doing it.
So basically NO not everyone will become good at hand filing that's fact.
The latest trend on youbtubes is to recommend everyone throw away their filing guides ya don't need em lol probably one of the dumbest things I've ever heard knowing the mess a lot would get there chains into. I hand file free hand no guides hand but I'm not silly enough to tell everyone to throw way what works for them and only do as I do, some even struggle with guides imagine letting em loose free hand.
Best way to teach someone how to free hand file is be looking over their shoulder you can actually gauge how competent they are and whether or not it's a complete waste of time.
I like guides as after some time cutting, my hands are not able to hold the file in the manner that I would like for good free hand filing, so guides it is.
if you can cut for hrs, and then free hand, then more power to ya, and go for it, for me, i like the guides, yes I can free hand when fresh, but after hrs cutting, i cant free hand the way I can when my arms and hands are fresh.
Love the grandberg file n joint for setting up a chain, or custom profile, found over time, certain combinations of guides on certain chains give good results for what i am cutting, some guides, not so much.
Again, match the chain to the timber and the chain/ bar length to the power head, and have at it.
Were all cutting different types of wood, different rainfall, and different rockwell hardness or balsa softness timbers, so there will be some variance with all of them.
find what works for your timber and enjoy it and being able to file to what gives you the best results.
edited to add.
it helps to add what type of timber your cutting, what power head, chain / bar combo when commenting as there are so many different types that one may not work for the other, and why, we all find that factory grind of a chain is at best, a starting point, and with some changes, can be made to cut far better for what we are each cutting, for those with soft woods, its a far different direction compared to those cutting hard woods, again add in the different types of timber, dead, green, rainfall, and region for what may work and what may not.