whart, 12,000 is a whole heaping lot of records! I can understand why you thinned them out. I have about a tenth that many, and that's a lot. Like most people, I will go back to certain records many times before I play a more obscure record. Some will never get played again. I think I played them all at least once when I first acquired them.
The more I think about it, my Moon 280D doesn't really sound "digital" to me, unless you mean by "digital" smoothing off rough edges. For example, I have a vinyl set of Starker playing the Bach Cello Suites and he attacks the strings with an aggressiveness that can be heard on analogue. On digital the vibration of the bow against the strings is not so "there."
On certain digital recordings with a very high sampling rate, digital recordings are almost like analogue. And, of course, not every analogue recording is great. Some are tinny and compressed. But with the best of both worlds, a very good digital recording at a high sampling rate and a very good analogue recording are extremely close even with my relatively inexpensive Moon 280D.
I think in order to be significantly better than the Moon, a digital front end would have to cost significantly more. I was running my computer into a Chord Qutest DAC, and when I compared it to my Moon 280D, the Qutest sounded much darker and less lively. I loved the Qutest when I first heard it, but I think having all the parts in one integrated box reduces jitter. And I'm guessing a DDC might have helped the Qutest.
But I play analogue and digital for different reasons. I write sitting in front of my Sonus Faber speakers. I play records while writing for a number of reasons. To my ear they sound better, but also having to turn them over forces me to get up every 20 to 30 minutes. Sitting too long is not good for my old body. In the afternoons when I am reading or writing things like this post, I play digital. I like exploring new recordings and new artists. I am listening to Dvorak's 7th Symphony which I also have on record, but this version is with Dudamel conducting.
In the end, as I think you suggested earlier, what matters most is having and fulfilling the interest in music. It's a very important part of my life. And I've enjoyed listening to recordings from my first Sears Silvertone portable stereo in college, through so many different pieces of gear I can't remember them all. The only constant is that I have continued to expend more $ as I have earned more money and my wife allows. Pretty standard, I'm sure.