do a blind test… personally, I enjoy more cheap, slightly warm dacs and transparent, powerful amplifiers
amp and dacs are resolved topics full of snake oil (just like everything related to this topic)
The healthy thing would be to have a variety of obviously different equipment without spending too much and use them to better fit the music you listen to or just for the fun of changing equipment
Oh, I have a walkman nw-a55 and I find its performance and construction disappointing. I don’t like the sound or the amplification.
I find Apple’s small DAC much more convenient and equivalent… although my favorite device is a generic external audio card connected to three simple amplifiers
The change for me is in trying headphones with different firms, although… when the right music appears, the equipment doesn’t matter much