Upgrade order? Preamp, amp, speakers

I tend to agree with Ejlif ,,very good advice!go out and listen to everything you can!Take your time!

Ejlif, I am leaning towards starting with the preamp, then speakers, then amp. So far I really like the Ayre K-1xe preamp. It gives a nice warm sound with great vocal dimensionality and imaging. I will also look at the Plinius M8. As for speakers, I have no idea where to start. The 802D with Ayre components sounded great to me. The Vienna Acoustics also sounded awesome though maybe a little to laid back for me.

Mapleleafs3: I have a Cary 303/300 cdp and a digital music server.

Any thoughts?

I think that the CDP is fine.
I never cared much for B&W speakers
Pre-amp can have a profound effect on the sound.
Speakers are the most "fun" since they are big and will have vastly different sonic signatures.

I own the K1x, and it is maybe the best piece of gear I've bought. I can highly reccomend it.

I also have the Parasound JC-1 amps and am using Von Schweikert VR4SRs. This is a nice match, I like it a lot.

Have to agree with Swampwalker's pithy statements.

My own notion is that, all else being equal, it will be more fun to listen to the new preamp through the old speakers than vice versa, so I'd do the preamp first.