reply to MaynardKrebs
Re: Ripping CD's - Mac vs. Windows I'll just reply to one small part. Personally I have ripped all of my collection on a Windows machine into Flac files which are lossless. You can also rip lossless with Apple Lossless. I would rip into one or the other and then as these files are still fairly large for a mobile device convert them to a lossy, compressed format for use on a mobile device. Ripped into either one of the the lossless formats first means that he now has his entire collection archived on a hard drive. I like the open format of Flac versus Apple having any control over my collection.
 +1 on ExactAudioCopy -- that's what I use also.
So if I rip to FLAC using ExactAudioCopy as the 'archival format' because it isn't controlled by Apple, but I make the decision to us an Apple device as the playback device for my blind friend, what tools do I use to convert from FLAC to AAC or to MP3 (I assume those are the formats a iDevice understands)?
Foobar2000 can do direct conversions from FLAC to MP3 (don't know about AAC, but I assume so).
Disclaimer: I have had very bad luck converting to MP3 using Foobar2000. I'm sure it's something I'm doing wrong, but I'm pretty up on these things and if I can't set it up properly without outside research it's not very intuitive.
What I normally do is use FLAC Frontend to convert from FLAC to WAV and then EAC to convert from WAV to MP3. Of course, this way you lose your tags. I normally go to WinAMP's "Auto-Tag" to put them back.
Another EAC user here. No need to convert FLAC files to play on iPod, iPhone, etc. Just download an app that plays the FLAC files. I use "Golden Ear" on my iPad to play FLAC files. Another app is "FLAC Player"
The problem I have is that my friend is virtually totally blind - he can just distinguish light from dark. So I'm leaning towards using Siri on an iDevice to let him voice-select his music, but I don't want to preclude using some other device/os if it can get him the accessibility to the music - hence ripping to FLAC and then transcoding for the playback device seems like the best route to take. So I'm not sure if using a non-integrated music player is feasible.
Being blind sure sucks. and what makes it harder for my friend is that he's a true audiophile - having had the best audio equipment ($25k speakers & fabulous tube amps) when he could see.