Wdrazek,
I've owned an Ipod for four years now so I'm not arguing for/against a product I'm unfamiliar with. I copy my CD's to my iPod in WAV format to avoid the audible problems evident with compression, but the iPod still isn't all that great sounding. Like you I'm 46 years old; I also work in semiconductors so the technology thing isn't a foreign concept either.
There are many that will argue digital is finally as good as analogue, no one will argue it's better (for what it's worth a decent analogue rig still stomps any digital source I've ever heard). And when I say digital source material I'm referring to store bought music in uncompressed format, not the "lossless" or "lossy" compression techniques that are used by Apple and others.
My reference point is my analogue front end, followed by several quality CDP's (feel free to browse my virtual systems), iPod doesn't even come close to even my kid's systems for sound quality.
You feel that high-end companion products ought to be offered up by the likes of ARC, BAT, CJ, etc.. The fact is you can't fix problems downstream: Garbage in, garbage out. Why create "music-first" products when the source is compromised from the get-go?
So.... some value ease of use, others will go the extra step because quality matters to them. Audiophiles are passionate about their music and as such, we forego convenience.