Yes and no. In my system I have found the best 6SN7 to be the old Brimar the second are a bunch of American NOS. I haven’t found a modern 6sn7 that sounds better than nos in my system. The best 300b I have had in my system is a modern Takatsuki.

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.

If you have a sufficiently high fidelity speaker set up and you can listen to music at whatever volume you like at any time you like, you do not need a high end headphone setup.

I don’t think you need training to enjoy the audio hobby. Just listen to stuff. If you are listening to a speaker system make sure they are positioned correctly and enjoy. You will figure out what you like over time. Then listen to other people’s set ups at meets or shows or at friends houses. You don’t need to sweat it.

Andy at vintage tube services in MI is also good. I use him and Brent Jesse