First off, you are going to like this and it is going to work a whole lot better then you ever expected. Be Happy!
Be sure to read everything on Gordon's site - a few times if need be - so it all makes sense and feels comfortable. Honestly, if you are at all comfortable with computers, this is truly simple but knowledge is power and at the very least will heighten your appreciation.
From a hardware perspective, the paradigm I have offered in previous posts is imagine you know have a perfect source for your system. So that part of the battle. and that set of excuses is over. Everything downstream of the Brick is all about analog audio as you know it. Cables, isolation, power, speaker placement and most certainly room tuning will all come into play and are required to optimize the potential of the new source. Take your time, its the fun part for most. Just know that whatever you hear Day One can only get better.
From a software perspective, there are a few things you can do to make life simpler - and IMHO ultimately better. First, I would buy a dedicated hard drive just for my music library (assuming you are going to have more then a few hundred CDs). Under iTunes Preferences/Advanced/General you will set that hard drive to be the iTunes Music folder location. (Dead easy just hit change and select the HD when it is connected) I named mine Bird.
EVERYTHING GOES IN THERE!!!!
Check (turn on) Keep iTunes Music Folder organized and Copy files to iTunes Music folder when adding to library.
The net result of all this is that everything you ever rip will always be exactly where it is supposed to be. Also, back-up, for which you must get another hard drive for is vastly simplified. Back up one drive and you know you have backed up all your music. BTW iTunes will also put all the album cover art on that drive too.
BTW I am sure like everyone else you are lazy about back-up. So don't go an buy that drive till you rip your first couple of hundred disks. If you are like most people you will decide that back-up however onerous is preferable to doing that again. Backing up once a month or even once a quarter, or after you add another 100 titles (assuming you are starting with a brand new high quality drive) is plenty.
Check out a Mac application called ChronoSync which will handle the mechanics for you admirably and ensure a better backup then you can get by just dragging files from one drive to another.
http://www.econtechnologies.com/site/Pages/ChronoSync/chrono_overview.html
BTW a real back-up, ohhhh that I practice what I preach, is one that is located in a physically different location - you are as much concerned about fire and water damage, theft etc as you are about drive failure.
Once you've set this dedicated drive up, you never have to think about it again. And of course you can access all this with an iPod too. Also, if you ever decide to add a Squeezebox once again you can point it at this single library. And if you want to go over to your buddies or wherever, just grab the one drive and you are on your way.
Enjoy the music!