[lextek]

i've been around for awhile. It was high end to use a PCDP ( portable compact disc player) with a line out. HD600s and RS1s were kings. I had the Headroom Max, Cary, PPA, MG Head, Melos, MPX , Audiovalve RKV and Steath. What awesome sound!
Now I have a Bithead with USB DAC. I stream my music from a Mac via WIFI. I watch my movies through Apple TV stream from" my Mac and listen to music too. It really is amazing what we can do.
I still use HD600s and Grado SR60s. Some things don't change.

 

[tattoou2]

LOL!  Yes, I easily can remember the Sony and Panasonic PCDPs I went through.  Like you, still have my Grado phones.  The more things change, the more they stay the same.

 

[Spareribs]

Well it can change but it doesn’t have to completely.

If you found the right amp, headphone and/or speaker and it’s to your taste, you really don’t need to “upgrade” or get something else.

Even old DACs can still sound great by today’s standards.

But if you’re gonna get back into buying new gear again, I would explore IEMs and portable gear since the technology has improved a lot in the past 10 years. The good news is that a lot of it is not too expensive or relatively affordable.