How good is good enough?

I am an audiophile. I want the very best sound I can afford and am happy to allocate a disproportionate amount of my disposable income to achieve this.
 

Typically I do an upgrade cycle every seven years and just really enjoy the music in between upgrade cycles. During the hiatus I stay up on Stereophile, The Absolute Sound, and HiFi+ as well as casually work on small positioning and tweaks to improve the sound. I also help friends put together systems and occasionally go to high end audio shows.

OP …”I’m just curious. When you arbitrarily upgrade your system every 7 years, do you hear a significant improvement each time?”

OMG, yes… enormous. Each generation has been such a huge jump. In fact, each component is a very real and substantial improvement.. It can take a year or two for me to do the upgrades. So, for instance I may start by the speakers or preamp… the jump is phenomenal. I spend enough time to get it broken in and appreciate the upgrade in itself before upgrading the next piece.

I a m not sure arbitrarily upgrade is quite right. It tends to be a function of my finances… although very subconscious. I enjoy my system and I think my subconscious keeps track of my finances close enough to tell me when, if I really stretch, I can make a substantial upgrade… which as I am sure you know, for me is to as a minimum double my investment in each component. When I in upgrade mode, virtually every spare minute is reading, evaluating, dropping by audio shops in towns I am flying through… switching into critical listening mode for a lot of the time. 
 

So, when compete, I have a system that is better in no small measure in every respect from its predecessor. I will say I have gotten better and better (yes, partly due to overall improvement of high end audio) at upgrading and the difference has become larger and larger with each upgrade. The last upgrade was definitely the very largest sound quality wise I have ever made. While the investment level was by far the largest, I feel that the ten years of season tickets to the symphony had significantly changed my goals and contributed to the success of this last upgrade. 

OP,

You bring up a really important issue. Once you upgrade, then you play music.

If you have a detail scraping system… you end up hearing the worst possible rendition of any recording… only the very best recordings sound great. If your system is musically oriented then most recordings sound great and the ones that sound great on a hyper detailed system sound extraordinary.
 

You have to be very carefully on the criteria you use to evaluate potential components. If it is the most details you can hear, then it is likely to end up, bringing out the shortcomings of every album and not it’s strengths.