Almost 9 years here on HF
Spent many $1,000's. Don't even want to add it up. It becomes an addictive hobby. At the same time it provides hours of euphoria and enjoyment from order point to anticipation of receipt to initial listening, etc...
I've learned what good sound is. I've learned what I like in a "sound" (this actually takes years IMHO) and there is tremendous satisfaction knowing you are listening to your favorite music on "gear" that makes the presentation better than what 99.9% of the general public is listening on. Some have no clue how good the sound could be and sound couldn't care less.
The most frustrating or wasteful part of the journey is buying same IEM's multiple times. Almost 1/2 of what I have spent on HF has been multiple purchaes (or going back) to a great IEM. I've bought some IEM's 3 times.
It's all really relative to a person's discretionary spending budget.
To this day, had my JH16's NOT had a imbalance issue, I THINK my journey would have ended there but it has not. Currently very content with my TF10's and JH5's. Having gone all the way to the top I can confidently say it doesn't get all that much better than my current set-up. When I think of "portable" listening in the late 80's with cassette Sony "walkmans" (which was an audio revalation/milestone in its own regard) and $10 earbuds....what we have now is literally 10-20 times better in every regard. I love it!
Among every IEM purchased in my history...JH5's are probably the best investment as far as a whole package (and I've owned JH13 and JH16). Well worth every penny I spent ($25 for impressions +$375 for JH5).
Having said that....when I come across a bundle of $$ I am thinking about UE11 or UE18. heh..heh...