Sounds like he needs to stop reading the Audio mags, and go listen a lot to systems at different dealers. For what he's paying to go thru that much equipment, he could fly to Overture or Goodwins, or any other number of dealers who are able to help him get a "synergistic equipped" system. I bet the dealers love him
You are not alone.
I have a friend who changes components on a weekly basis.
In the last year he went thru the following speakers-Magnepan MMG, Kef LS50,and now has a pair of Joseph speakers.
He has also gone thru numerous amp, pre-amp, integrated and phono stages in the same time frame.
Something he doesn't change are his wires.He's not convinced they make a difference.Same goes for power tweaks.
I've mentioned that maybe this practise is what is the root of the problem with his short term romance with any new gear.
I would say he gets more enjoyment out of the chase than with the listening experience.
I enjoyed the sound of most of his set ups, some were steps up, some down and some just sideways.
He always convinces himself that the new piece is better than the last was, but the cycle continues.
He has bought some new speaker wires and a power cord, but I haven't heard the results.
The wires are not expensive,not Cardas or Nordost, but better than stock,or so it would appear from what I've read about them.
He has all the time in the world to listen to music on his system.That may be part of the problem.
I've told him that whenever he starts to nit pick it and look for some reason to trade and try something different he should just pack it away and buy something from a pawn shop and listen to that for awhile.
Then when that grows weary, re-insert the better gear .
Then decide which one makes you happy and stick with it.
Familiarity can breed discontent.
It can believe that.