Are all Audiophiles masocists?

To answer the question it's almost certainly more pain than pleasure for me!

A jump has us thrilled. 

But how soon before the system is driving us nuts and we are only living for the next upgrade or tweak that will remove those little niggling things (that we weren't even aware of before the last upgrade) which are driving us crazy.  

Every true Audiophile I know is almost certainly certifiable.  😇😇😎

Net/net It's a toss up between OCD  and masochism. 

After years of just work and family, I’m glad to have a hobby again.
The obsession factor helped pull me in and forced me to learn.
Now that my system is assembled, I’m turning toward expanding my listening.
Obsessing about hearing more and different music will, I hope, take the place of the "dragon chase" for better sound.

Because at this point, the sound is so good that I really don’t have a good reason to spend time the rig rather than the music.

When I start posting about problems with my rig, I'm sure to be called a hypocrite! I'll just quote Whitman at that point: "Do I contradict myself? Very well then I contradict myself (I am large, I contain multitudes)."

I think we all do this with other parts of our lives: we have a good job, we think of better jobs. We have a nice car, we think of getting a better car. We have a nice house, we want a bigger house, and so on. I'm perfectly happy with my little system but I like to experiment and try different things with it. It's a hobby. I also dabble with model trains and I'm always adding things, running new locos, new scenery. It's fun but I don't look at it as 'never being happy.' To me, it's just part of the hobby itself. As long as I'm having fun, its all good.

you poor .......

She's beautiful, right!

curious, what do/did you do for a living?

Does doing what you enjoy immensely often make you a masochist? Depends, I suspect. 

Obsessing about, changing systems is no more a "problem" in audiophilia than someone obsessing about collecting media. Mediaphilia, imo, can be as aberrant as obsession over the gear. I am certainly not weird, but Mediaphiles can be weird!  ;) 

I used to flip gear in search of the One, the perfect speaker/system. The masochistic aspect of it was self-imposed budget constraints, attempting to reach SOTA with a very modest budget cap. What's the definition of Insanity? (Please, I know the phrase; it's not necessary to respond to this rhetorical question.) 

I finally woke up and realized that I never would be happy that way. I began to cultivate a collection of equipment to allow for variety of experiences. It has been a near perfect solution to RES, or Restless Ear Syndrome (my phrase to describe the condition of upgraditis), which can be carried out at the same cost as plowing money into an ultimately unsatisfying search for the One.  

I get bored without progress, and I love the challenge of advancing a rig continuously. I also thrill to hear a performance become more engrossing, emotionally fulfilling, over the years. There is absolutely nothing wrong with that - as long as there is integrity in my relationship with my wife, maintaining my charitable giving, and I'm not blowing the rest of the budget.  YMMV