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?
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