Trip, if you feel the need to rebuild your system, or even to analyze it, here are some hard learned tips I've come to embrace after many years:
1. Start with your speaker choice. Typically, your speaker selection will more strongly dictate the characteristics of the range of upstream electronics than any other component choice. Some speakers are fairly forgiving and get along with just about anything, while others do not. For example, I'm partial to Thiels, and this forces me to keep a close eye on high current delivery and relative warmth from everything upstream. Like Avantegardes? Then the spectrum of flea powered SET amps is available. The key word should always be synergy - look to balance the relative strengths and weaknesses of your components against your listening preferences. BTW, I think the B&K is ok with your Silver 5s.
2. Once you have found a speaker/power amp combination that works for you, then look more closely at the front end. While it can be critical, if you're budgetarily strapped, I would rather cut corners on the pre-amp stage as opposed to the front end. An integrated amp is sometimes a good alternative under these circumstances - and there are some very good ones today. Better front end gear with their better output stages can sometimes get by with a cheaper (and sometimes better) passive pre.
3. Next look to cabling to fine-tune any residual shortcomings, starting with your speaker cables, then interconnects from your front end forward. While I've found it's OK to mix speaker and IC makes, it can become quite an art to intermix IC brands in the same system. Cables can be quite vexing, and places like the Cable Co can be very helpful here. Cables will not fix a fundamental mismatch elsewhere, but they can screw up an otherwise fine system if poorly selected. Look to cabling to compliment, not correct your system, and you're on the right track.
4. Don't overlook your power supply. Start with a simple 20 amp dedicated circuit, then look to good conditioning for the front end and upgraded power cords throughout, starting at the amp and front ends. If you need power from your amp, I've found that superior dynamics result from going straight into a dedicated circuit outlet.
5. Tweaks, such as vibration control and room treatments may come next. These can bring some noticable improvements, but unless severe (hard floors and glass everywhere) I wouldn't turn to them until more fundamental electronic issues are resolved.
When making changes, give your system at least a week to settle in (longer if new components are involved) before making any further changes.
I'm a big fan of having a vacuum tube somewhere in circuit, especially with digital, to add smoothness and warmth. You can also roll tube types to further fine tune the sound. Looking at your situation and budget, if you want more warmth and like your speakers, I'd ditch the Denon, MSB, Pioneer combo and go for a warmer, tubed output, one-box CDP and a passive attenuator pre. After that, I'd turn to your cables, depending on where you need to go from there.
Alternatively, you can do as Sean has suggested, and experiment with just cables - but depending on just how bright your system is to you, I think this amounts to band aid audio under the circumstances.
Again, these are just my opinions on how to do high-end, and others may have a different view.
Good luck to you, and remember that this is all supposed to be fun.
