Maxing your 'Pod'tential
Lane, you're missing true enlightenment in your life's quest! ["Mission: iPossible," April 2005]. I find myself on a similar mission to yours; even leveraging the same resource as you, and having access to the collection of all metro-area libraries via the Internet has sure made it easy to track down titles from a broader collection than just what the local branch has on the shelves. Yet your pursuit of "volume" short-circuits your mission. You'll have your favorites buried under even more filler. You've got a mammoth haystack covering those elusive needles!
I'm afraid you've got to roll up your sleeves and become a music critic. Treat this as a mission to track down all those old favorites that you never did buy, and also to use www.amazon.com and other resources such as www.rockdetector.com to check out "recommend-ed related artists." Then, you have to methodically listen to the whole CD with a critical ear to cherry-pick those personal favorites. Put only those on your iPod.
I use my two 35-minute commutes for this each day, and it's why I have a boom box in the kitchen while I cook. I put a sticky note on the back of the jewel case to note the good track numbers for the next rip-ping session. Despite the occasional slog through some pretty bad CD-filler, it has much improved my commute over listening to "morning show banter" -- especially when NPR is in the middle of fund-raising.
True, this is a slow process. It's taken me four years to get to 2,000 songs and, in the early days, I didn't have a portable device to listen to the fruits of the labor on the road. Now, though, I have the wonderful experience of saying "I love this song!" no matter which track pops up. I even enjoy "shuffle shock" now, especially if the player selects a track I haven't heard since I ripped it months ago. It might take me from traditional Celtic folk straight to Slipknot and then to Clay Walker, but at least I like all the songs. It also sometimes creates some pretty compelling mash-ups: try Gregorian chant followed by Black Sabbath's "Children of the Grave" or a classical requiem followed by Eminem's "Lose Yourself." But it will only work if you like both pieces.
If you walk this path, you won't reach your goal in a hurry, but what "life mission" isn't more about the journey than the destination? Anything worth doing is worth doing the right way.