I buy headphones for their unique drivers and have an interest in hearing subtle differences in each, so I don't regret it as the amusement comes from learning.

I don't buy top tier headphones as they will still be just another headphone, but I could've gotten multiple for the price of that one unit.

From trying many, I've learned that for sheer music enjoyment and accurate reproduction headphones are limited by their very nature, speakers are more complete sounding and IEM's have better tonality than headphones.

All in all I don't think expensive headphones are worth it, for just sound enjoyment.