I apologize if this has all been re-hashed ad nauseum.

I wanted to listen to audio books in my car, which led to an MP3 player, which led to me starting to rip the ~600 CDs my wife an I own. About 200 discs in, I came up with the idea of going 'disc less'. They take up so much space, get scratched, and I can't let my 2 year old in our room because it's the first thing he goes for. I'm not an audiophile, and I don't really listen to music that much anymore, so I don't feel compelled to keep a library of CDs if I can burn a CD-RW or copy to an MP3 player at whim.

To this point, I had been using Windows Media Player 10, MP3s, at 192 bitrate, which I vaguely understood to be close enough that it is unlikely I would ever know the difference. But I had some nagging concerns, so I started to research the issue further online. That only led to more an more confusion about WMA/AAC/MP3/CBR/VBR/codecs/softwares/tags/playlists/libraries/etc. Thus, I'm lost.

Here are my issues:
1) EAC/LAME is really slow, WMP and iTunes rip fast.
2) It doesn't seem I can get EAC/LAME to auto-rip when I insert a disc. WMP and iTunes will (and will eject when done). This is terribly important for ripping 600 CDs.
3) EAC/LAME uses freedb - which seems to suck bad. Both iTunes and WMP recognize the fairly obscure DJ mix CDs I have copious amount of, but freedb doesn't. I have no desire to be double checking every rip to make sure it has the right info, and even less desire to be typing in artist/album/tracklistings. Good integration with a db (and library - WMP lays out the folders nicely with album cover picture embedded in the folder thumbnail, iTunes library browsing seems a bit slow over my LAN) is important. I like being able to rip all my discs without even having the monitor turned on - just walk by and stick a new one in when the old one has popped out.

So iTunes seems to have the same set of convenience features as WMP (and the 'approved' hard core audiophile software seem to have none of them). But I have heard repeatedly that iTunes has a bad MP3 encoder. On the other hand, at least iTunes has VBR, which I understand should lead to better bang-for-your-byte audio quality; WMP does not. Ripping into AAC/.M4A is an option I suppose, but I'm not very keen on that idea, as it will be a barrier to ever using a non-iPod MP3 player. I haven't investigated RealPlayer.

Now, I realize this is something like asking Mexicans: "Do you think Taco Bell has good food?" but can I progress on my plan with Windows Media Player in good conscience? What I am saying is, convenience is more important to me than the purest audio quality, utterly. Given the convenience level I insist on, what should I use to rip? How probable is it that I will ever notice, and care about, a difference between: WMP MP3 CBR 192 vs. WMP MP3 CBR 256 vs. iTunes AAC 192 VBR vs. the original CDs vs. <your recommendation here>?

Thank you for any advice.

If convenience is paramount to you, WMP 10 is your best option. As you mentioned, hardly any other program integrates album art fetching, automatic tagging, renaming and folderizing as it does. As for quality, you can determine the bitrate appropriate for you by doing ABX tests using foobar2000 between a ripped WAV and an MP3 of the same track for different bitrates of the MP3. Although I use WMP to manage my music library, I rip to WMA and have never used the MP3 encoding option, so I have no idea how good it is.

Well, it already looks like you've made your decision not to use EAC, which is the only secure ripper (you can always ask more about it when you start to notice skips in some of your mp3's).

THe only way to answer your question about the encoders is for you to do some listening tests (ABX).