There are all kinds of nasty rumors out there about ripping a redbook CD to ALAC using iTunes on a PC. I think I would avoid it.
http://www.computeraudiophile.com/content/iTunes-ripping-ALAC-may-have-bug
Perhaps you should consider using EAC with AccurateRip. Either directly or inside one of the many PC-based players that use it. Why bother with Windows Media Player (except at work where they force you to use it, I guess) ... use one of the major thrid-party programs instead. You know the list (Media Monkey, FooBar, dbPower Amp ...). If these are not familiar to you, GIYF. There are many fine tutorials on EAC available, btw.
I rip my archival copy to WAV, then create a FLAC -8 (again, either using FLAC directly or usng one of the major players) to capture and store all the metadata and album art. I like to store the cover art in the music file itself, I usually use the cover from the CD Single if available which is way more fun than staring at the same album cover all the time if you use the directory approach). MuvUnder Cover is FANTASTIC at this, and a little known program. And xrecode II (also not well known) NEVER messes up any metadata when making ALACs or making compressed files for your portables. Neither of those 2 are free, btw, but the authors deserve some money. FooBar, by way of contrast, loses the embedded album art
For some reason, I have often found that up-sampling a 44.1 redbook track to 96, then "decimating" it to 48 for making an ALAC, sounds better on an iPod than anything else. I think Apple naturally prefers the 48-96-192 world to the 44.1-88.2-176.4 world. Who knows.
Lots of people Rockbox their iPods and then use FLAC for everything. This won't help you at Work where you can only use WMP -- so take the WAVs there. WMP will supply its own metadata and album art when you play the files. Use your lovingly created FLACS (created with one of the major programs) from the EAC-created WAVs on your own PC (with the same major program you chose).
Convert to a compressed AAC or uncompressed ALAC for you Apple portable devices. I would use xrecode II and then load them on the device with XPLAY3 (also not free) and never install iTunes, but what do I know? Even my wife uses iTunes and won't consider anything else depsite hours of lectures from me, complete with a PowerPoint presentation on the real meaning of the Nyquist folding freqency (don't believe what you read here about that -- you do NOT get a perfect reconstruction of every music frequency from 22.05 down even though you sample at 44.1 -- that's a misunderstanding of reality) and some example Fourier transforms (my bride has a PhD in Math Stat from Princeton). And she just bought a Mac, so I will now be foobaring alone, just like when I was single.
Your phones may require MP3's ... again, any of the major Windows players will make these perfectly. And if you do it right you can be sure that all the metadata in the FLAC shows up in the MP3.
You kept score correctly -- I have a WAV, FLAC Original, FLAC upsampled to 96, ALAC, and MP3 version of every track. So what? They are all named perfectly and in the right directory. I back up the reference WAV and the FLAC with the metadata. Yea I know only the FLAC is really needed. But it all happens nearly automatically. 3 TB disks are $199 on Ammy. USB 3 is blazing. And there is nothing more important to me in my non-work life than my music collection (other than my family of course).
Good luck, and enjoy.
Edited by wavoman - 10/22/11 at 3:39pm