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I think I might be too attuned to the enjoyment of newer, virtuosic guitar playing which is branded as folk music but is really divorced from the tradition of carrying a tune - American primitivism or very personal and despondent blues. I'm not saying that there is much validity to how someone's life affects their art either but I can hear something irreplaceable in certain songs that seems to be shaped by a tragic experience that I cannot at the moment hear in this
The story behind the creation of the instrument and the longevity of its use is very endearing to me though

It's not editable and I should've perhaps posted this one

I'd 100% argue that someone's art is effected by their experience/tragedy. It has been noted many times. There is for sure an irreplaceable quality. That said, something can be "good" by whatever aesthetic standard you please (taste), without it, but the medium in this case matters quite a bit. For the blues, the irreplaceability of tragedy, often makes or breaks it, and I fully get why you posted the examples you did. Because it is an African American genre, it helps to be black, and to have grown up poor in the rural South, though sometimes whitey pulls it off.

Jimmie Driftwood grew up poor in rural Arkansas, but the sense of exclusion that you hear from black artists is notably missing IMO, except in bits and pieces, such as the song I posted (Lefthand Side of God). That is interesting in itself, because I get the sense he had a bit of a chip on his shoulder about organized religion (can be heard in the track "My Church" which is 2 tracks Past LHSoG on the same album), and it would likely qualify as an alienating vector of his life, given his time and place.

For further example, compare two versions of the same track written by Jimmie:
I find it interesting she says in that intro that Jimmie was one of the most beautiful people she ever met. Still, Odetta from Alabama is the clear winner in terms of "soulfulness", whatever that means.

That all said, there are many things to enjoy in any given bit of music, and technical-skill is not to be disregarded. It is perhaps outside the circle of your listening, but there is endless debate in the Jam Band world about whether Jerry Garcia of the Grateful Dead or Trey Anastasio of Phish is the better guitar player-- Jerry, from a struggling working class family, or Trey, a middleclass well-to-do from the Northeast. Anastasio is clearly the more technically proficient player, but Dead-stans, being largely morons, have a hard time articulating the value of soulfulness.

My point here is there is value to both, and it isn't some kind of sin to appreciate the one or the other, as they are not mutually exclusive. The amount of beautiful and well made things to appreciate in this world, and the multitude of reasons why they are enjoyable, never ceases to literally amaze me

Tangentially: Odetta's Battle Hymn of the Republic is the best version I have found from modern times. In my estimation, her refusal to change the lyric "let us DIE to make men free" (often changed to LIVE for some ridiculous reason), is a big selling point.

I have also found Paul Robeson's versions of Stephen Foster minstrel songs to be a lot more compelling, (certainly better than B*ng Crosby versions) but that is another can of worms.

could the soulfulness be gained or lost tho? a lot of artists that have gone mainstream seem to have lost the authenticity behind their music but at the same time musicians who have been mainstream forever have, towards the end of their lives released the most authentic sounding albums. from top of my head come two examples, cash and cohen. cash's version of we'll meet again from his last album still sends chills down my spine and sounds much, much more authentic than even his first singles.
i'd lie if i said that last albums made by old farts before they died wasn't one of my favourite genres

I did not know this We'll Meet Again existed. It is very good, just like most of the other stuff he did in this period with Ric Rubin. Johnny was a very sick man in the 90s. This article is long, but it provides some good context for it: https://www.vanityfair.com/culture/2010/02/johnny-cash-201002

I did like some of his earlier stuff, but I found it more hit or miss for sure. That late period it did seem like he could almost do no wrong though. To the question, I would say yes, it is entirely possible to gain or lose a sense of authenticity and soulfulness over time, depending on what any given artist is doing and attempting.

yep, late cash was his peak and the most soulful of his records and it transcends genres. country, folk, sacred harp hymns or industrial rock he nailed every song he did in that period

this convo is lovely, and making me sad my comp crashed out n i lost my bluegrass banjo bookmarks...

as an aside re:instrument making i have an odd fondness for different woody stringed instruments that is... difficult to articulate?
i remember high school orchestra teacher once voiced it, in a sense where when it comes to "fullness" and "depth" of sound the full size violin is the only orchestral stringed instrument that produces it. that the full size viola would have to be the size of a cello to produce the same fullness, etc.
there was another violinist in class who had a black violin made out of darker wood and it had more unique depth to the sound.
when i retire and move into baba yaga cabin in the woods i am going to make a violin that sounds like a banshee when played

that may all sound slightly mentally deficient but you can definitely hear the difference when the 'a' string is played on the cello or viola vs a full size violin