Is This the Essence of "The Audiophile Dilemma?

It is not an all or none proposition. 

First of all, most of us have no idea what we are looking for and I do not mean this in a bad way. Most of us have limited exposure to really great systems and you do not find them at dealers regardless of the equipment they use. There are a few dealers who do a great job. I could probably count them on the fingers of one hand. I would bet more of us have been exposed to live music than great systems.

Second of all, most people buy a system and have no intention of climbing an audiophile tree. This includes some audiophiles. They have found what they are looking for.

The rest of us have found part of what we are looking for and just have to make a few improvements. This is the incremental group. We know what we are looking for and will get there eventually given the availability of equipment and finances. I do not know about the rest of you but I am loving the ride. 

@roxy54 , Not one of mine either.

What dilemma? 

May be inevitable at some point in system building. Certainly experienced this on my journey to finding what I was always looking for.

One great advantage newer audiophiles have over us oldies is digital has improved so much over the years. My reference for audio has always been top notch analog/vinyl, digital never had a chance back in the day, didn't stop me from trying.

Live music is your guide, and patience your friend.

I think it’s very difficult for people to feel secure in their choices. I was a conservatory-trained musician and I also had my own music production company, so I know what I like when I hear it. Doesn’t make my taste more “correct” than anyone else’s, but it does make me confident in my choice. I can see the dilemma of the average person who hears all these reviewers talking about how great everything is, so they buy it and can’t understand why they don’t love it. IMO, the answer is to work with a good dealer or consultant who will help you find stuff you like, but as said above, these people are scarce nowadays.