How does your digital music sound? What do you do about it?

Neil Young made some waves (in my head anyway) last week talking about Steve Jobs being a digital music pioneer but listening to "records" when he went home. I have no evidence of that one way or another even though I did hang out with Steve once in his favorite audio porn emporium in Palo Alto (the Audible Difference). I know he didn't like "tape", but never heard him talk negatively about cd's.
Have heard the similar refrain from Peter Gabriel who surely knows a thing or two about making music sound good.  

I have been told that lossless (which I use as much as possible) is equivalent to a redboard cd (which is good but not great). I'd like to get some feedback from folks in the know. Or not in the know...Maybe some links and comments about what you hear and what you do about it..

For years I bought master recordings and them put them on master tape to play in the car. They sounded great. When I plug my iPhone into my car and crank it up, I'm sometimes impressed (even with 320kbps) and sometimes not so much. It seems to me that it's all in the preparation and UE. Like apple computers, the specs don't necessarily determine the performance..or perceived performance.

I have ears.. played music professionally from the time I was 8 until I was 25 and then was a concert promoter and tour manager. Left the business long ago but my ears could tell who was out of tune in a 100+ piece orchestra and they still don't like laptop speakers (etc.).

4 years ago I started the process of putting a 4000 cd collection onto servers. Backed them up and backed them up again ..and again. Had moved them 3 times and just didn't want to do it again.. We are starting to do the same thing with books. We are near 60 and have accumulated a lot of "stuff" along the way. I got rid of the turntable in the early 90's and will not go back. Most of our listening is casual. So, please tell me what you have found and what you've done. Appreciated..of course. Thanks.