Weakest link - a different question?


Google shows a fair number of posts to this forum where people ask "Here's my system, what is my weakest link?"  As an engineer, to me the more important question is, given system X in room with acoustics Y, how do I tell what the weakest link is?"  I'd love to know what methodology people use to determine what component or room treatment makes the most sense to upgrade next given the sheer complexity of interactions between room, amp, source, speakers, power, and cable?
Can any of you distill out from your experience what process you used when deciding which component from your system to upgrade? I'd love to hear your stories of _how_ you made the decision for your system.
(For the sake of background, I have an entry level British system: Rega Planar 3, Rega DAC-R, Rega Elex-R, Spendor A4s, Chord interconnects, QED speaker wire, and a Panamax power conditioner purely - because we live in rural PA where the power is dirty - but I am not asking about my system, it is the methodology that interests me).
Thanks!
wqgq_641
Post removed 
An excellent question. In my case I combine a multitude of approaches:

1) I compare results listening via speakers with listening via my very revealing Stax electrostatic headphones. Headphone listening, of course, takes the room, the speakers, and the power amp out of the picture.

2) I compare CD and LP playback, using the same recordings to the extent possible.

3) I do **a lot** of research and reading.

4) I only consider upgrading when a broad sampling of what I consider to be credible reports about a particular component causes me to become particularly excited, and suggests to me that the upgrade is likely to provide an improvement that is more than marginal.

5) I try to avoid components for which either user reports or technical considerations lead me to believe that the component is particularly critical with respect to setup or system-matching. Increased criticality of setup or system-matching can only increase the difficulty of identifying a weak link.

Also, for that matter, I avoid components that seem to inspire controversy with respect to either performance or the manufacturer’s customer service. Alternatives are usually available which can be counted on to not entail such risks.

6) I trust my technical instincts, as an experienced designer of sophisticated analog and digital circuits (for defense electronics, not for audio).

Regards,
-- Al
@almarg thanks, your first two points make eminent sense and I hadn't identified those strategies so clearly. The rest, yes, I'd reached similar conclusions.
It is an excellent question and sometimes difficult to diagnose.  After many years in this hobby, I believe strongly that the speaker/room interface is the most overlooked item in creating a system.  IMO, in a normal domestic environment where speaker placement is limited, there is absolutely no way to tell how a speaker will work in your room without a home demo. I have had many very good speakers in my room including Totem Forest and Hawks, Harbeth Monitor 30 and SHL5s, Coincident Partial Eclipse, Opera Callas Monitors and now the Trenner & Friedl Pharoahs.  Each one worked to a point, but when I put the Operas up it was like magic.  The speaker worked perfectly in the room and those small speakers filled the room like a concert hall.  So the problem is - how do you do that?  IMO, either get a dealer to allow you to demo, or buy used, hope for the best and sell if they don't work out.  But once you get the speaker/room thing together, everything sounds a lot better.