Well I think of it as having different road-blocks. Like some of mine have been really obscure and individual to me, so there's no guide that I would have expected to cover it. It can be a bit of a lonely road in some ways.

The issue with the information out there regarding super-O is that beyond the basics (such as breathing and relaxation), the "advanced skills" as shared are just so different that I find them sometimes counter productive

Sometimes you just have to experiment, throw a lot of things and the wall and see what sticks. Some new technique or mental model might not be the big break-through thing, but it might produce a different feeling or cause your body to respond in a new way... and that might be a puzzle-piece.
Funnily enough though, the most interesting experiments I've had are the basics, revisited. For example, finding out after years that I'm not really as relaxed as I thought I was... that I'm holding tension somewhere in a way I'm not even conscious of, or I have a level of mental tension where I can't surrender deeply enough, or in some particular way. Or every time X happens I do Y reflexively. Or I'm completely dissociating and not staying present enough in my body. There's a lot of detail you can drill down into, but sometimes you find these things when you're not looking for them. And trying out different techniques or tactics can be a way of shaking that tree and seeing what falls out.

As a novice to prostate play, I'm actually pretty satisfied with my progress made so far. I can now pretty much reach a few dry-O's within an hour every session and with varied sensations.

Well, that's what has kept me coming back. As long as it's more novel and satisfying than traditional masturbation, then that's enough to make it more worth using than not. Then eventually, you'll have a session where something new happens that you weren't even trying to do. I swear that'll happen, even if you never change a single thing about your current technique, something will happen in some slightly different way, your body will respond in some way you didn't think it could, and you'll be like "What the hell was that?!". I've had that happen more times than I can count. And sometimes that new thing feels completely game-changing.

It's just that my sense is that I'm still far from anything I could call "super" just yet, and I don't know I'm on the path to it.

I'm not sure there is a path to it exactly. I mean there have been cases of people hitting intense orgasms early on, then not being able to repeat those successes, so I guess anything can happen. So I don't think you need to graduate to it, like completing a series of Karate belts and working your way up. It might be more a case of figuring out how to get out of your own way, and maybe you'll do that accidentally without even trying to.