I'm taking votes

Could be heartbreaking when you find out that your LP12 beats out your $20k CD12. And I think your speakers are good ones also. I would recommend getting a new Shelter 901 cartridge to replace the aging Troika, and spend the other $18500 on mint condition record albums, which will always be valuable collectors items, as well as wonderful music. CD's will be in the Goodwill bin next to the 8-Track tapes, when the next digital format finally takes hold. Older LP's are even now, skyrocketing in value, and will continue to do so. With analog, the LP's gain in value, and better TT's hold value well. With digital, both software and hardware plummet with each new advancement in technology.

Gear comes & goes, but MUSIC stays. So I partly second the motion to buy music (preferably LP). However, as you'd like to influence the SOUND too, and given YOUR system, look into speakers first. You want fast speakers, neutral with an articulate bottom end. To better the WB, a speaker with slightly different drivers & design philosophy could do the trick; Kharma, big Piega, Acapella, are only some such offerings... I don't recommend stats because I never successfully matched the older Klouts with stats -- your amps may be different.

This way, you'll renew the sound and also have new music to listen to!
Later, if the digital f-end is still a question-mark (assuming you're happy w/ the LP12 set-up), hit the market... Linn universal, Lindemann, AA, Accuphase, etc, will be beckoning you.

I'd say change the Cd elements but try the Linn or give it extensive listening before sinking 20K in digital playback. Perhaps you can see great improvements looking elsewhere for a combined 20K in speakers and digital. Sounds like more fun in the hunt in this case.

I would take a different tack and ask what is it, in what sounds to be a great system, that you find lacking? If you know what you arer trying to fix, you have a better chance of being successful. Having said that and at the risk of disagreeing with anyone (not my intent), the following are worth consideration:

1. What is your biggest source of music? If it is digital then money in that direction makes sense. The only problem is the rapidity of change in the equipment. Since you can audition the lindemann for 30 days its probably a safe way to go and 12500 less than the cd12. If you wait for the new linn universal you will pay top dollar. There are a lot of fine players now and you may get bigger bang for your buck than the cd12. If you have a lot of lps, your analog set up could certainly be helped IMO - verdier, vpi to name a few - with a better cartridge.

2. Rooms are worth treating and one of the more cost effective tweaks - but only you can tell this.

3. Speakers - Only heard the wilsons once but there are a wide variety of great speakers in that price range. I used to hold that source was the most important but have been a lot more impressed with how important having the best speakers (ie the ones you like the best) are. I have piegas which I love (and do not sell), I believe the new or old models worth a listen but this is the most subjective and biased position I will take. If you find your system lacks vibrancy you might consider a major change like horns (avant gardes).

Food for thought, I hope. Good luck