Now this could get me flamed but I would not put speakers first. Your source is very important preamp/amp , then speakers. I'm not saying that your speakers are not important, but componets have electronic signatures they all sound different. So if you go and by a 5000 dollar pair of speakers, your going to be SOL, if your speakers don't match well with your componets. SO if you start building your system with ok speakers whats the worst that can happen, you have a great sounding system that will sound better when you get new speakers, or you can have a terrible sounding system that you can't stand listening to because the speakers you bought show off all the flaws in your componets. As for new CD or Transport/Dac, I can't help you on that. It's a toss up, but prehaps you should forget the Pre amp, take that money get a great DAC with volume control and cut a step?
Order of importance
I recently upgraded my system to Thiel 2.2, CJ MF2200 and CJ PFR. I went back to using my old Denon 1520 CD player from a new DVD. I was told by a salesman that the order of importance in a system is 1)speakers, 2)source, 3)preamp, 4)amp. Therefore, I was told to buy a new CD or use the Denon as a transport and get a DA converter. Any thoughts on this and what DAC to consider?