Many people have made the switch from CD to a flexible digital library and traded quality for the convenience of inferior formats like MP3. You don't have to. You can have that nice fat bitrate lossless CD quality with all the convenience of a 10000-track CD jukebox. But first you have to rip those CDs...
So you want get that music off CD into digital format. The plan is to only do this once. Ever. So the key question is:
"Do you want it fast or do you want it good?"If you just want any old quality of rip, use iTunes, Windows Media Player, etc. If you have an expensive CD/DVD ROM drive, a shiny new CD and a bit of luck, it'll rip fine. The problem is, something like iTunes will just sprint through a CD regardless, and if it picks up any errors, well you might just hear them when you play it back. CDs aren't perfect and don't have the best built-in error checking, and it takes care or fancy hardware to reproduce them exactly.
If you want this to be the only time you ever rip this CD, ever, consider a slower error-checking rip. CDex is good, DBPowerAmp or acknowleged leader EAC are better. You're looking at 20 minutes a CD, but a good chance of perfect rips. EAC will do a couple of things to get good rips - read and re-read (extremely slowly if necessary) every bit of data on your CD, and then compare that to a crowd-sourced database to determine whether there are any errors on your copy of the CD.
So you have a CD/DVD-ROM drive and a stack of CDs just waiting to be ripped. If you have a laptop (or when you realise some CDs just won't work well on your current drive) you might also want to look at getting an external CD drive or getting that old tower out of storage instead of just relying on that one drive. For major bulk ripping sessions, start with a pile of CDs, set several drives going and burn through your collection.
So basically, you fire up your ripping software, feed it a CD, get it to pick up the tagging information, then start ripping and come back when its done. The best format for filenaming is a "Music\Artist\Album" folder structure, tracks named and numbered "01 - Track Name" for sorting.
If your library software needs a playlist for each album (most don't), make sure you spit out a ".m3u" file at this point.
Some rippers, such as EAC (think DBPowerAmp too) can grab the artwork as part of the tagging process, saving you some work later.
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