When does analog compete with digital?

Syntax,
You need a PS-X9 with the remote. I finally found one for mine.

Naim gear has long been known for its ability to reproduce music with its original rhythm, energy, and forward momentum intact. Some analog gear (Linn, Rega, Roksan) is also known for this quality. When you said you "still feel like something is missing" when listening to your analog source, my conjecture is that your phono stage, and possibly your turntable/cartridge combination, is lagging in that area. I don't know what dealerships and product lines are available to you locally to audition, but the Dynavector P75 I suggested is widely marketed and is a product that does not mess up the temporal qualities of music. Same with the P3-24, which is most often paired with Rega's own Elys 2 cartridge or with the DV 10X5. I don't know that this is the missing factor for you, of course; it's just my best guess.

...when it comes to more complex music, I much prefer the analytical sound of digital, which is more clear and 'in your face', so to speak.

FWIW, the opposite is true in my system. On music of any complexity, regardless of genre, my vinyl setup challenges the clarity of my digital, exceeds it in presence (if that's what "in your face" means) and demolishes it in terms of low level detail, micro-dynamics and harmonic complexity.

My system differs from yours, obviously. My pretty decent digital player retails for just $2K (+ another $2K for interconnects). My vinyl front end retails for over $20K.

Why this particular ratio? Why not a $20K digital source and a $2-4K vinyl one? Because IME my ratio provides better sound for the money.

No digital front end I've heard - at any price - can approach a really good vinyl rig. IMO this is because the two systems are flawed in fundamentally different ways.

Most vinyl flaws are generated during playback, which means they can be reduced by user involvement (better setup, better gear). OTOH, many digital flaws are inherent in the medium and cannot be reduced by the user for any price.

Further, with vinyl the performance ceiling has not yet been reached. No vinyl replay system in existence is capable of extracting all the information in an LP groove. Despite my seemingly crazy ratio, there are upgrades that would take my vinyl rig's performance even higher. Analog sources contain enough musical information to allow changes in even a high end playback system to make real improvements.

So, as others have said, the better question would be, "When does digital compete with analog?" IME the answer is, "When the analog playback system is of a low enough level so that its (avoidable) flaws outweigh the (unavoidable) flaws built into existing digital media."

PTM hit it on the nose with the multiple components fact of life in analog. I think we all have a price threshold that we psychologically are willing to spend on a component. With analog, over time, we can get up to that level on multiple items cartridges, tables, arms, phono stages, and cleaning. Before you know it, you have a considerable investment because it is in pieces.

I have a problem with the concept of "competition" between formats. I need both to enjoy all of the music I've collected and I expect both to deliver a high level of performance. Also, my system has been assembled so that, on a basic level, both sound quite similar.

For classical music, I listen primarily to CDs. Very few current releases of classical music are available on lp, so collecting CDs and SACDs is the only option for new releases. I appreciate the long, uninterrupted playing time, the lack of ticks and pops in quiet passages, and the ability to easily find my place in the libretto for operas when using CDs. The other factor is that most of the classical labels are actually doing a better job now with recording quality than they have done in the past (e.g., DG) which is a far cry from most popular labels which are making crappier and crappier recordings these days.

For rock, jazz and other popular music, I listen mostly to lps. Particularly with older recordings, lps most often sound much better, in all respects, than their digital counterparts. To me, it doesn't matter if it is a case of one format being superior to the other, or poor digital mastering or degradation of the original master tapes, etc.-- it just is simply the case that most often the lp sounds better. Because most popular recordings do not have the dynamic range of classical music, surface noise (clicks, pops, sputtering) become almost irrelevant with popular music.

When I am doing a demonstration of the very best source material, it is almost exclusively lps. I've never heard digital sources match the dynamic impact of well recorded lps, or have the same kind of vast, open and realistic soundstage.

Because there are so many more components to lp source components, I have spent more on those components, but, my CD player is no slouch (Naim CD555).