ghdprentice,
I am in a similar place as you are, except all of my gear is fairly modern TOTL CJ tube equipment. I too have a well appointed modern LP12 and it is sporting a Grado Aeon 3 cartridge. Although I have just North of 3K vinyl LP's my wife laughs that there are really on 50 or so in regular. The sound is wonderful. However, in the never ending search to get my digital (currently using Cary DMS 600) closer to that of my analog set up, I have earmarked $15K- $20K . That may sound lie a lot to some people, but my LP12 has that amount in it without the $6K cartridge included. I have two other TT's: a new Rega P10 with a Transfiguration Proteus D cartridge, and a Nottingham System Deck with a Koetsu RSP. At 64 years old with a progressing retina disease, I find it easier to have several TT's set up which I can swap in and out rather than changing a cartridge on a tonearm. From an ease of use, and an economics view point, digital gives a good bit more value.