what is a lazy old audiophile to do?

I am an old audiophile. Left behind by technology. I'm tired of replacing tubes, want convenience, if not simplicity (maybe simplicity). I decided to put my CD's on a computer hard drive and play from there. I have a new Pioneer SC-07 ( I know, not audiophile), new Imac with all the latest, Kef 205/2 speakers. The only connection from the Imac to the receiver is the headphones out from the Imac - (tiny). I have no idea why Apple is so uninterested in audio. I may send back the Imac and get a Dell with sound card and HDMI out, which I can connect to the Pioneer. My question: is this stupid? That is, am I trying to do something that will never satisfy my ear? I care a lot about the sound (have a thirty year old pair of Snell Type A's in the other room that I love). Can I get decent sound with the convenience of the computer? How? I don't really care about surround sound or movie crashes; I just want really good audio through my computer.