Hey Cat6man,
The Server is in the reclocker chassis, so you get both with the server. The reclocker is not immune to jitter, it merely attenuates it, and does a very damn good job of it. So the rule applies. The better the digital source, the better the sound.
The Server will give you more improvement than anything. The digital source is most important. No question, and it will sound like you have a new front end entirely. It is that good. If you want the best performance, get the Server. You can get great results using any digital source into the Reclocker, but for the little extra costs, get the Server, then you have both. I have never found another digital source that beats the Totaldac Server. Not even close.
What you gain by moving up to the Monobloc DAC's is quite simply, more of everything. More drive, more transparency, more separation, more dynamics, more depth, more focus, more slam, more more more good, and nothing bad. This is quite a significant upgrade from the D1 Dual, especially if you wish to drive amps directly. If you get the server, and at some point want to upgrade to Monobloc or Twelve, have Vincent put 2 AES outputs in it so you don't have to send the server back when you upgrade later.
Now, depending on the quality of the preamp you use, as the Twelve really must have a good preamp, the Twelve is amazing. However, it does have one weakness, and that is drive. So it is not the best to drive most amps directly. Depending on ones system, tastes, etc. one may very well prefer the Monobloc DAC's to the Twelve.
Hope this helps.
Paul