There isn't a simple answer I agree. It's a point of irritation to me that often so called objectivists; of which I consider myself to be, will insist on missusing the saying that measurements can tell the whole story of how a collection of electronics will sound to the listener.
What measurements can tell you is how a piece of equipment will perform. There is a lot of evidence that suggests that equipment that measures to a particular set of criteria will sound better than equipment that doesn't.
The word synergy isn't really very helpful when it comes to audio reproduction. Making sure each componant can work correctly with the other componants in the chain, which can only be done through measurement is the synergy of an audio system.
The listening space as you suggest has a huge impact on how a sound reproduction system will sound. Only measurement can tell one what areas of this need addressing.
But, what measurements can't tell one, not yet anyway, is how the listener will percieve any changes to the system.
It's the listener, rather than the equipment, that we can't measure adequately to fully predict their response to a particular sound.
There isn't a solution to the listener who states "if it sounds better to me then it is better". The reasons it may, or may, not sound better are irrelevant in this case; one can't argue with the statement.
This big disadvantage for those who adhere to the view the statement states is they are bound on an endless journey trying this and trying that, all at some expense, until they find a setup that satisfies all the criteria they employ to judge the betterness of their system.
I don't like the sound of the Harman curve on some equipment. With some equipment if one rectifies one deviation from the curve (Harman in this case) another problem can arise elswhere particulalry with loudspeakers in a room.
Have faith in the measurements is all I can write. True they won't tell you everything but they will tell you how each piece of equipment performs and that is an excellent starting point. One can look at the measurements, accept that say the Harman curve is the current standard of proof for listener preference and rule out equipment that does not meet your criteria. It's a lot easier than trying to get a meaningfull demonstration at a sales outlet (Hi Fi dealers/consultants) are sales outlets) or borrowing some friends kit for a few days.