High End System Building. How important is the matching, cabling and room? Thoughts ?

The room matters a lot, do everything you can afford.

Yet the next step is most important .... do not buy anything unless

a. You NEED it. How do I know? Because you are BOTHERED and can NAME the ISSUE you wish to SOLVE

b. You have done an A/B in your space and you PREFER the new thing, FOR SURE.

From here it’s never ending. Hopefully you will go many years with a set up, but you may not. When you have amazing Speakers, Amps, Cables, DA etc ... then you might in time be bothered and fine tune it with AC cables perhaps, Fuses perhaps, Caps and Resistors perhaps.

The better the system the more obvious is any small change.

Small gains are often costly ... that’s the reality. Do you need them? See #1

A great thing can be costly or not.  A bad thing can be costly too.

Enjoy the Process. For the Audiophile the system is the creativity, the instrument.

@patrickcarey 

"best advice I can see on your audiophile journey is to try some stuff make sure there are returns or at the very least if you buy it used that you'll be able to flip it and sell it to someone else if it doesn't work for you so you're not risking a ton of money. "

With an unexpected divorce, followed by an unexpected retirement and a suddenly "fixed" income, I use the same methodology. The key is having the patience to put the time in to research and locate what you want. And to get it for a price that allows you to flip it if need be.That being said, if I am sure about something, I don't mind buying new.

@tony1954, @ghdprentice

Glad to read you have a similar experience.  Your methodologies are good.  Great sound is certainly a measure of personal taste, and ongoing tuning over time. 

Everything is a component. All the interconnects and hardware as well as room acoustics. 

I'll be digging into some UNobtrusive acoustic treatments in my future.  Might have to move to have a dedicated sound room :)

Another thing of huge importance  is the quality  of the recording. Or of the lp, cd, radio broadcase. 

@calvinj 

As I’m sitting here reading all this, my mind wondered to room treatments.  Have you measured out the first reflection points on your front wall and ceiling?  I to have a doorway next to a speaker and it noticeably messes up the sound, but I covered up my fireplace and put a 2’x4’ absorbing panel above it and for the other side, I bought one of those cheap folding walls and tossed a comforter over it. I have to take it down when company comes, but that’s easy enough. The only thing I haven’t been given permission for, is to put panels on the ceiling,  but I’m thinking you might have to really consider it. Oh, and those smaller corner bass traps, do help a bit. ( but once again, they were not wife approved here.)

All the best.