I wish I hadn’t have discounted iems, since I now use them much more than my over ears, even when I’m at home. I also wish I had have had a better understanding of the type of sound signature I preferred, would have saved myself a lot of time and money. That being said, I did enjoy the journey itself to finding my end game 🙂
What I mean is if disturbing roommates, spouses, neighbors with high volume is not an issue AND your speaker system is good enough, a home headphone rig is not necessary. On the go, I use AirPods. No one can hear the difference between high end and low end while commuting or grocery shopping. I am glad to have owned some of the best headphones and headphone amps ever made and I’ve listened to just about every good headphone you can get up to about 2010 (when I quit serious headphone listening). If I put the headphone money into my 2 channel system it would have been better spent. That’s the advice I would have given myself back in the day. I still own HD800S, HD600 with the marble finish, and a Dennis Had IHA1.