With all due respect, what you demonstrated was not the difference between digital and analog. You demonstrated the difference between playback of a particular digital version of that material on your digital system path, compared to a particular analog version on your system's analog path. I believe you when you say, that you and the GF preferred the analog playback. I just don't think that says anything about digital and analog playback in general.
Yes, if that were the only time this had happened it would be the act of conflating the media capability with the one single anecdotal experience. I've done this demo many times over the last 30 years, and often at audio shows. One of those shows (RMAF) we had the designer of the DAC we were using, which is one of the very best DACs I've heard anywhere (Stahltek, and better be good, it with the transport together were over $70K) in the room. He was playing stuff off of his hard drive and I realized I had the same thing on LP in my box of stuff I bring to shows. I offered to play if for him; after 5 seconds he turned to me and said 'digital has such a long way to go..." I've always taken his pragmatic viewpoint as why he made such a musical transparent DAC (and the fact that he was a brilliant engineer didn't hurt either).
Another standout I recall was a woman who was deaf in one ear and about 50% in the other. She was easily able to tell which was which. In this situation I was using an older Linn setup, which might be considered quite ordinary today, but it was better than 99% of what the world's population was able to hear at the time.
That this is such an easy demo to do and consistently goes in the same direction does say something. Maybe we have exceptional LP playback- many people do not (I found out decades ago that phono preamps can generate ticks and pops if you aren't careful in the design and I think that is what has driven so many people crazy, no realizing that it wasn't the media doing the ticks and pops). But whatever it is, its an easy demo. Not
proof, but an awful lot of
evidence. Mind you, I prefer how easy digital can be and I like the fact that its gotten so good in the last decade in particular. Enough that I 'almost' don't care which is better. I just like to play music. But its easy to arrange a demo, and I've yet to find a digital setup that really beats out the analog side, so I'm open to anyone being able to show me something new. That's just not happened (yet) so for now in my world, there is no means to show how digital is actually better, but plenty of means to show that it isn't.
This suggests to me that if the digital media is really that good, that the playback apparatus still has (for most people) a very long way to go, this for me despite having access to some pretty high end stuff. So maybe in theory its better, in practice it rarely works out. One should be careful with stuff like this because the bias can go both ways. One thing about analog, you get one thing wrong and the whole thing goes down the loo. The turntable has to be speed stable, physically dead, the platter has to have a mat on it that properly damps the LP itself, the pickup can't have chatter in the bearings or the arm tube resonating and talking back to the cartridge body, the mechanical resonance correct and so on. Once you have those ducks in a row analog really shines. With digital these days its very different- you can get excellent sound from a $12 DVD from a pawn shop driving a $125.00 Topping DAC (E30, for anyone counting). But its always that last nth degree that makes the final difference. (yes, I know Topping makes better DACs- we use a D90 in the shop. I really like that when the design is really sorted out, that something that inexpensive can have the high end manufacturers shaking in their boots. I really want music to be there for everyone.)