I consider that this hobby is too much every time I consider making a new purchase. This includes the $13.88 shipped that I paid for my KSC75.
I was happy with my music. I enjoyed just listening. Using my iPhone and stock buds playing mp3 files that averaged 192-256 bit rates (...and I've done worse...), or just on my laptop speakers. Or my wife's 4-watt(ish) boom box if I want (gasp!) more SPL while I'm cooking noisily. I still do this regularly. But now I have a growing collection of cans and FLAC/ALAC and a bucket list of future gear. It's harder to be happy. And happiness in audiophilia with regards to acquiring devices usually comes and and then subsides like a drug fix. This is certainly true within my current will-buy price range of ~$300 for headphones (a little less for amps), where I don't expect that the gear is not going to knock your socks off, and by logic is likely to still be true if I climb up to where returns are said to be diminished. I mean, if you bought a TOTL, and are still talking about what aspects of your music another piece of hi-fi is reproducing better than yours, it sounds like a lovely problem to have, but it's kinda sick in perspective.
Most non-audiophiles can hear the difference between your gear and theirs; of those, most won't care enough to experience a change. Beats owners, when they defend their purchase against the best of your mid-fi, probably prefer their sound. People who are coming from stock buds would clearly benefit from anything from Sony to Senn to Beats, but some won't make the move. It is my belief that we as audiophiles are not any better off than them. The people who aren't interested in upgrading their sound probably have it best, followed by the people who bought Beats and will not move on to, say, our gear. I envy that about them.
This hobby is too much. Sometimes I get out of it. Then... well, you know.