I've always been satisfied with my system(s), I don't need dissatisfaction to spur an upgrade; it's the joy of discovering what more my system is capable of that motivates me. My enjoyment of the music is a constant.
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Simple answer to your 1st question - I often change components out of boredom - gives me something to experiment with for a few days and sometimes I find something that significantly changes my system (better or worse). Being cheap, I spend far more time on fine tuning set up/room acoustic's and rolling tubes.
Not so simple answer to your second question - If you truly love music, and listening to music is your real goal, you'll enjoy music over a car radio, a boom box, your home audio system or the seat furthest from the stage. For some of us who do, fiddling with audio components and set up is a totally different hobby. Both are very good ways to pass the time and they co-exist quite well for most folks.
Personally, I spend far more time on music, both in listening, studying, and collecting. This is far more rewarding (for me). I spend about 95% of my time allotted to audio/music to music, 4% sharing experiences and helping out on line, and about 1% fiddling with components/set up.
IMHO folks who are suffering from "audio neurosa" are still on the steep part of the learning curve of the audio hobby, and have not yet realized what it is that they want and what is really obtainable (or not!), let alone how to get it.They are still relying on superficial recommendations of well meaning folks and eager (for a commission) salemen, proceeding without sufficient independent critical analysis and then suffering disappointment when the expected miracles do not occur. But they learn, or burn out.
>>What is the longest time you have been totally satisfied with your system?
I had a HighEnd system for almost 14 years. I had bought it with the term "HighEnd" in mind which means to me: as good as it gets regarding my budget and sane senses. I only changed this system to my current gear due to a move into a bigger house. My living-/listening room has 64 squaremeters now with a high wooden ceiling and wooden floor - a dream to make music in (my Steinway Grand and my Hammond A 100 are in the same room). It's very clear that music-REPRODUCTION also gets all the benefits from this room. And again I consider my system high end and I cannot think of any reason to change any of the units except they were broken. Knowing the fact that music reproduction NEVER will come anywhere close to live music I am more than happy about what this system can do for me. Real music, however, is something completely different - hence I don't get the thread's title right.
I think it is possible that some people could be looking in one place for one set of rules and an expected outcome, and then without even realizing it really find what they were looking for elsewhere, completely by accident or fate, and never really know what that was even as they are somehow set at ease. Maybe a part of that was in the structures of music or the mechanisms of components and systems, until the whole of it was stumbled across elsewhere. Ultimately I do not worry about it. I will change and walk away. And I will probably relationalize it to death. The one sure thing in my relationship with music is that I do not feel any need to justify my likes or dislikes. I can be moved by the silliest shit, and left cold by pure genius. I really like that.
I phrased the thread very carefully. I think you have touched on the operative thought in that the intrinsic knowledge that reproduced music can , but will never replace live performed music. But you will agree, that Steinway grand notwithstanding, you are no Horowitz...hence our compulsion to acquire a system that will reproduce the feelings we had when we heard him live.
I'm not implying that I am one of the dissatisfied audiophiles. My system core has not changed for a long time.
Newbee, although i am new to this, I am rapidly realizing that you have some valuable insights.