Hi everyone . I believe I am not the only one going through this, and will seek to pursue more and more , a never ending “struggle” for me or anyone one here 
Let’s share our experience and journeys here . Thanks !!!
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I do not experience much in the way of upgrade itist. It is all too easy to get involved in upgrading one’s hifi as an end goal and forget the true end goal.
I upgrade infrequently I have in the past had the same amp for 20+ years. I have had my turntable for over 35 years although upgraded in part over that time. When I do upgrade it tends to be in bursts to maintain balance in the system.
The end goal for me BTW is to sit and enjoy the music I have no interest in listening critically all the time thinking what could be better. I just want to enjoy the music.
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Reading this forum is the best way to ensure a healthy dose of upgraditis.
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Absolutely. I am learning when to “stop” pursuing … it’s a bad habit😅for me , very poisonous so as to say . Never ending …
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It’s just like any interest. Look at petrol heads, never content with going for a good drive, always bonnet up, remapping etc!
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When to stop? Available finance I’d say.
There’s no such thing as “too much money”.
That’s a statement for you (ahem). 
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In the photography world it’s called GAS, Gear Acquisition Syndrome, the pursuit of the perfect camera. I suffer a touch of that along with Upgradeitis, the pursuit of the perfect hifi system. It’s a 40 year journey and it’s not quite over. I do have rules though, nothing bought without something sold and always buy used where possible, I find the symptoms a lot more manageable that way.
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I thought I had reached my end point a year ago, then tried a NVC TT phono stage and it gave the TT such an uplift I bought it. The downside was that the LP12 sounded so much better than the streamer side of my 222 that I always felt streaming was a poor second. Then I got an opportunity to buy a 332/333 ex-dem and I now have two equally balanced sources and am very happy with my system. No current plans to upgrade further. I won’t say I have stopped but paused, how long the pause is remains to be seen.
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There comes a point where the next upgrade is a seismic jump in cost e.g. 552 to Statement S1 or NDS to ND555.
That’s my real world stopping point.
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Unscratched itches. Ever since the Swiss Cottage show in ‘83 when I heard a LP12/Ittok/AT09 with a Meridian active setup I’ve wondered about how good an active system would sound in my room. And the ATC thread has done nothing to relieve the itch. And then there’s the ATC SCM20 ASL limited, how would they compare with my 300/Titan 500s?
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One should stop when funds are not available in the first place (@MikeD already said that).
However I also believe that one should stop, within his possibilities, when he doesn’t perceive any results when changing gear. What’s the point of spending lot of money to get, let’s say, a 5% benefit? Also newer/different gear doesn’t always mean it’s going to be automatically better.
Be confident and spend money only when you are really sure and happy with the results you get. This involves patience and a lot of tests.
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@ Blacknote … One day we shall start a nordost thread to discuss and learn from there 
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Actually I’ve thought of that too hahah 
A Nordost thread should be started sooner or later!!!
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I have been having thought constantly - if one day I get to the NC 500 or lucky enough , statement (if it’s still under production by then ) , and after that , what ? and if I get to the reference or flagship of a certain make , be it cable, streamer etc , what comes next? The road never ends. Guess novelty plays a part here too
I suppose it depends what your goal is. If you’re a “best of everything” type of person then the journey may never end. Personally I like bang for buck so am satisfied with my lot. Another house with bigger listening room might change my tune but right now I’m content.
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…when the purse is empty…
My purse emptied once in the 1980’s, my system has stayed the same to this day, except I have sold stuff (and added some stuff to the computer sound).
Perhaps learn when to be content (always easy to think greener grass is in the next field).
However reading about systems here it seems I live in a desert…
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I can no longer afford to spend money on HiFi so my journey has come to an end. I’m happy with the system it’s well balanced and has the sound I was after that had eluded me for years. Everything is fully serviceable so I should be able to keep it going for years to come. I spent a fair amount over the years chopping and changing and often ending up disappointed. No one can tell you when to stop, you do need to take a step back sometimes to be able to enjoy what you have. Turn it off for a few weeks and do something else. When you come back to it you might think differently.
Try speaker positioning before changing out any equipment it makes dramatic changes to the sound and it’s free!
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lol … that’s what I did at certain point for my NC… and when I add on something , I play around w the toeing I guess many are doing so too
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I suffer from both 
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