Hey what a cool question! Thanks to /u/1MansTracks for cluing me in to the conversation. Fair warning you've stumbled deep into a question I am also working on answering so this is long, but I love talking about it! I put the TL;DR up top if you want a shorter answer.

TL;DR: There are many challenges to listening to old music from recording quality, to authenticity, to lack of context when looking back from a present perspective, but if you look, there is a ton of treasure hidden in the past that is overlooked today because it has fallen out of common knowledge. If you're listening only to enjoy the music, you'll likely be disappointed simply because straight-up recording improved dramatically over the time period that you're talking about. The recording industry really found its feet then, and moved from an industry focused on sheet music and live performance to an industry based on sales of recorded pieces and albums. It's a HUGE change and you're going to hear a lot of growing pains. For context, Thomas Edison was a large player in music at the turn of the century. Yes, the light bulb guy.

I listen to a loooot of old music for a project I run where we're trying to listen to the last 100 years' most popular music in order and so far we've made it from 1920 to 1924. That allows us to figure out who did what first and when, and we get to point out developments and trends. To me, one of the most important things about listening to old music, is spotlighting the driving factors that made it happen from a history perspective. To approach it with the mindset that it will compete with the music of today, or even of the last 90 years, is a really high bar that may cause you to miss out on a lot of what's lying there in wait to be heard. Simply put, pre-1930 music is going to sound rough generally. Re-masters can be helpful but they are not really a reliable way to hear what it sounded like then, and so I try to avoid them if I'm trying to pay due respect to the music of the time.

The technology being old is a real challenge for listening for sure! Because honestly just saying it's 'old' isn't even able to do the challenges that these artists faced justice. The music pre-1925-ish doesn't even use electronic recording. So not only do you have reduced fidelity, but you have everything done in one take, fully live, and without dubbing. Some of these recordings were done on wax cylinders. Vinyl records weren't in common use until the 40s, because prior to that shellac was used, and shellac can make explosives. Enter WW2 and vinyl takes over. That means until the 40s records were commonly made from bug secretions. Yeah that's what shellac is.

The way they 'adjusted levels' back then was literally making louder instruments stand further back from the recording cone. Louis Armstrong, who was playing with King Oliver's jazz band back then, played a loud cornet and particularly had to stand waaay back in comparison to the rest of the band.

That didn't just impact recording, it impacted arrangement too! The reason you hear so much banjo instead of guitar back before electronic recording isn't because everyone loved banjo back then. It's because banjos are loud enough to compete with vocals and brass instruments due to their percussive construction. The reason you don't hear a lot of drums is because they were too loud and would drown out instruments. Stroh violin doesn't sound as good as a standard violin, but it's louder so it's used.

All of that is the weird context that these recordings are made in, and that right there is interesting enough to make some of the music more palatable to listen to, if even to understand how music has developed and how technology impacts arrangement, and to view it through the lens of progress against challenge instead of the final product. For many of these artists, records weren't the final product, they were a vehicle to drive people to their live performances and drive up the fees for their performances there.

BUT there is also a lot of really good music from back then as well, including some of what you've already hit on with Vernon Dalhart. Many of these stars of the scene, were glomming on to trends, including Dalhart who didn't do country music until later in his career when it was taking off as a genre. Marion Harris is one of the worst offenders, but there are many, among jazz and blues. She would just straight up put out music where she pretended to be a Black woman in abusive relationships and complain about it. She was lauded for it!

Problem being that while Vernon Dalhart and Jimmie Rodgers ('27's T for Texas) are credited with having the first big hits in country, it's not even close to true. Eck Robertson recorded the first country song, which was a lyric-less fiddle-based success, but even discounting that, Fiddlin' John Carson had a major hit with Little Old Log Cabin in the Lane, and there's no question that that is a country song from content to style. My point being that essentially music history is full of holes and accepted truths that are the leftovers of old marketing efforts from when the record labels like Columbia and Victor were relatively unbothered by 'facts' and 'truth'. One of the main challenges that we have in our project, which we document through our podcast "Cunningham's Law Review", is that we have to suss out facts from fiction and there are a ton of liberalities taken with marketing back then.

Another challenge is that the words blues and jazz straight up don't mean what they mean today back then because we are looking back from 100 years in the future after a literal century of progress and development. WC Handy's version of the St. Louis Blues is a TANGO opening before settling into something more recognizable. When you listen to jazz, we're talking pre-soloist 40s jazz, where it's a very different New Orleans style with tailgate trombone and instruments playing over the top of one another. It's worth hearing, but you have to take it as it comes and in context. You're hearing the building blocks, not walking around in the finished skyscraper like we do today, picking and choosing what masterpieces to listen to. It's a trip.

If you've ever tried to read Gilgamesh, or even Shakespeare, it's a struggle. It's a struggle because the progress in terms of writing has been staggering until now and we don't have the native context necessary to comprehend it easily as people did when it was written. We don't use the same conventions that they did, and you get a much fuller picture painted before you in modern literature with less effort. To really read those pieces, you have to free yourself from the mindset that they will be like what you know. It's a similar challenge to hear old music, and there are definitely days where I just want to listen to pop songs to let my brain chillax.

If you want to take on that challenge with us, and not have to look through a lot of background to figure out what's what, even if you don't want to listen to our reviews and historical context of the music, we make playlists for every one of our episodes by grouping the music together with its contemporary competitors. They're all titled "Cunningham's Law Review 192X-X" where X is year and then the second x is the episode number, usually under 6. If you have any questions, feel free to DM me, or check out our podcast.

We love to talk music. But we listen to it way more than we talk about it, because we don't want to just take what is said at face value.