I initially got into records because they quite frankly sound better than digital when you are listening to all analog record (no digital steps), mastered by a top shelf engineer, and pressed by an audiophile label (Analog Productions, Blue Note etc.). I got to say, the more I have gotten better (and more analog sounding) DACs, the smaller the gap in sound quality has gotten. It has gotten to the point, I’m now very reluctant to pay premium prices for out of print records (something I used to do without much thought).
Getting well pressed reissues is expensive business, and used records are a crapshoot. Before delving into vinyl solely for the sound quality, I would suggest thinking about getting a DAC that has the timbre and resolution that aligns more with your taste. To get a vinyl rig that matches sound quality of your Dave, you probably looking at spending $15-20K; it might make more sense to put that money towards getting a higher end DAC. Finally, if you mostly listen to music recorded from the early 80s onwards, I wouldn’t bother with vinyl because you are simply listening to a digital file pressed on plastic; my rule of thumb is, if it’s recorded digitally then listen to it digitally.