Upgrade order? Preamp, amp, speakers

I would suggest starting out with a tubed preamp. You have a nice cd player and pretty respectable speakers, so I would suggest upgrading the electronics. Since a preamp changes the system sound more than the amp in my experience I would suggest a good neutral tube preamp, like a Herron VTSP-1A, a BAT VK5i, or a CAT SL-1 MkII or MKIII. Just a few ideas, but more than anything have fun and buy used. That will save you from expensive mistakes. Happy listening!

To that list of tubed pre-amps, I would add Joule LA-100 & First Sound Presence Dlx.

How about a goal that your system is so satisfying you don't feel the need to upgrade anymore? I found that analytical multi-driver speakers like B&W (which are way better than most IMHO) make you dissatisfied. Maybe when you get to the point of tiring playing around with stuff you could consider Spendor S6, orS9. At least they crossover above 5kHz. But for really satisfying sound try single driver full range like Brines FTA-200 or carolinaaudio.com Jordans.

I'm just suggesting you keep an eye out for these 2 speakers and audition them when you can. Listen for 1/2 hour at least and the sound will grow on you vs. blow you away the second you hear them like the B&W.

With your current setup, I never liked Parasound digital amps. Try Classe, Musical Fidelity, or Jeff Rowland amps. Speakers are tough to buy and sell being so big.