If you are talking about playback hardware it would have to be my vinyl rig hands down. As a matter of fact I think I have spent more on accessories for my vinyl rig (The VPI RCM plus various alignment tools, scales, stylus cleaners , strobes, fluxbusters etc.) than I have spent on my entire CD setup.
However a big reason for that discrepancy is that since I have never heard a CD digital setup that sounded better than playing equivalent vinyl (sorry Paul, but that includes your hi res digital rips) I chose not to pursue the higher end digital (and higher priced products. In my mind, since I would be looking to pay vinyl when looking for the best sound, it was just not worth the money that it would have cost to get a more state of the art digital system.
Not that my digital system sounds bad by any stretch, I built is around a solid well respected DAC, the Eastern Electric, and am very happy with it. But if I look at where my vinyl and digital systems sit on the quality spectrum, the TT is much higher along the curve (compared to what else it out there in the market), so it is not surprising that it cost me much more than the digital equipment.
Now keep in mind that these decisions and the commitment to the vinyl format were made many years ago when digital was limited to the 44.1K Redbook standard. As the hi res digital markets matures I may have to revisit some of these choices. It is quite possible that native hi Res files (as in those made directly from master tapes) very well could sound better than vinyl. I will have to wait and see. Of course at that point It will not only be a matter of whether they sound better, but also of what is available in those formats. Of course just like vinyl, not every hi res files will have better sound, only those made with care from original sources. I'm sorry, high res digital rips of LPs by definition cannot sound better than the original LP, at best they can only sound the same. And with a huge amount of the music recorded over the past 20 years or so being done direct to 44.1 digital for CD release, I am not sure if there is any benefit to releasing them in a higher res format. Of course analog tapes will benefit greatly from high res mastering, but just like with audiophile LPs, not all albums have good quality masters available to start with.
When and if enough hi res releases become available that sound better than LPs at that point I might rethink getting into higher quality digital. (of course they would have to be high res files of albums I want and do not already have good sounding vinyl copies of already.... Hmmm, that could be a problem
).
I guess the bottom line is when I get to the point where I can and would use the digital system more for audiophile type listening, then I will consider investing more in it. But until them it's still LPs for me. (perhaps when Tidal starts streaming high res files next spring I might start to get swayed.