Dude, for the amount of cash you are willing to spend, it would be crazy for me to even begin to tell you how to start.

If it was me, I would want to have a dealer's backing for my purchases. Also, it's a place to go should a problem arise, etc.

Take the CDP out of the equation for now. You may not be able to listen to specific combos of gear, but most dealers will have simliar stuff in terms of performance, so you could supplement.

I like the idea of the PSB Imagine, so why not start there and hook up amps in your range. The Imagine sound great and are easy to drive making them a nice rock choice. Once you have a pair of speakers, you can take those to the audition of a specific amp if need be.