New source versus pre-emp

I’m looking to upgrade the 2 channel aspect of my system and would like some opinions as to where I might begin. My thoughts are that I will upgrade my digital front end and add a dedicated 2 channel pre-amp. My current system consists of a Levinson 39 going into my Krell HTS 7.1 (direct bypass) and into my Classe amps. I have connected the 39 directly to the amps but didn’t care for the imaging nor soundstage as much in that configuration. I plan to make this a long lasting investment (OK, poor choice of words since audio equipment is certainly not a good investment), so I am willing to spend pretty good money to get the best equipment I can afford. I will upgrade one piece now and then the other in the next year or two for fiduciary reasons.

My question is where should I begin, digital or pre-amp? My collection is mostly all redbook so SACD or DVD-A is not necessarily a requirement. Although, I do think for the $ I might like capability of high rez playback, but not at cost of sacrificing the redbook performance. Multi-channel audio doesn't really interest me anymore. Based on my research, the digital components I am looking to evaluate are the EMM Labs setup, the Reimyo CDP-777, Wadia 861se with the GNSC Statement mod, Audio Aero Prestige or Capitole, or maybe look for a good deal on used dCS Verdi/Delius here on Audiogon. The pre-amps could be VTL, VAC, First Sound, Supratek, or similar. I want a IR remote so the EMM Labs or H-Cat is out, and I’m thinking I’d like to give some tubed equipment a try.

My thoughts are that the pre-amp is definitely the weakest link currently and I could start there. Even though I do run mainly my CD player through the pre-amp, I can use the good pre-amp for other sources as well. This also gives yet another year or two for the hi-rez battle to settle (or fizzle) out, although since I’m mostly interested in redbook I’m not stuck on that issue. On the other hand, if I choose to buy one of the players that has a good digital/analogue volume control I can really look around at the various pre-amps if necissary. While not SOTA anymore, the Levinson is still a decent CD player and I’m pretty satisfied with it up to this point but I know they've made significant improvements over the past several years.

I’m sure many have been at this point in their system building and would like to hear your opinions as to which direction to take, and why. By the way, I live in an audio wasteland pretty much and have virtually no dealers within 300 miles so auditioning all, if any of the products is likely not possible. Thanks.
I would start with a pre-amp, bang for buck thing. Very little difference between digital source as a $$$ amount per sound quality improvment.

If your happy with the Classe amps and they are up to the job as far as your speakers go...the best tweak is at the pre-amp IMO.