I know it's presumptious of me to post a how-to guide, but I'm getting bored of the same questions being asked, and the same mistakes being made.
Starting point: you've got a huge pile of CDs
Desired end point: some kind of digital streaming system, playing your tunes
I'm not going to go into playback hardware; PC, Mac, Squeezebox, Sonos, Linn DS, whatevs. In my opinion the only real way they differ is in their user interfaces and expansion capability. They're all digital systems, so the only thing that's going to make a significant difference to the sound is your choice of DAC.
What I'm actually after is your approach and choices regarding ripping your CDs to files, so you can play them on your new system. The overall aim is for you to rip once, and never again, rather than getting half-way through, discovering a problem, and starting over.
This is not an unbiased, equitable guide. I have opinions, and I'm going to spell them out.
Finally, I don't want this to go on for pages and pages - stop me if I get boring. So without further ado:
Lossless versus Lossy
Lossless music file formats are just that, lossless representations of the original CD. Exactly the same digital data as the original CD. Lossy formats sacrifice some data for smaller file size.
The most common lossy format is mp3. mp3 comes with different settings, measured in kilobits per second, the higher the kilobits, the more data, the closer to the original, but the larger the file.
You probably call yourself an audiophile, or at least you're interested in good sounds and music, that's why you're here. Do not use a lossy format. Use a lossless format. If you rip to a lossy format then information is gone for good; you can always transcode down from lossless to lossy for a given application, you can't go back up the way. I'll say that again: USE A LOSSLESS FORMAT.
Compressed versus uncompressed
On the assumption that we're using a lossless format, the three biggies in this arena are FLAC, ALAC and WAV. ALAC is owned by Apple, and is really only useful for Apple kit; namely Macs and iPods. There is also the Microsoft Proprietary WMA lossless, but support for this is severely limited so I'm going to discount it right now.
Lossy formats effectively compress the original data. BUT this does not mean that all compression is lossy. FLAC and ALAC are lossless, and compressed. WAV is lossless, and uncompressed full fat. The usual comparison made is to a Word document (the WAV file), and a zipped copy of that Word document (FLAC or ALAC). If you unzip the file all your words are still there. Compressed is different to lossy.
As we're all aware, disc space is very cheap. Resilient, managed space is less cheap, but still not going to break the bank. iPod space is limited and more expensive, so for your core system (assuming it's not an iPod) the compressed versus uncompressed debate is a red herring.
Tags / Metadata
Tags are chunks of information, embedded in your music files, that describe the file. Artist name, track name, track number, album art, all that good stuff.
FLAC and ALAC support tags.
WAV does not.
Nearly all music management programs maintain their own database of what is in files. So for instance Windows Media Player and MediaMonkey will be able to tell you what is in a particular untagged WAV file because you've told them. If your untagged WAV files become detached from the life-support-system of the player, say through a software malfunction, or you simply decide to change player software or hardware, then you've lost all context of what is in them. Tagged files carry data about themselves around with them, so it's simply a matter of telling the new player to go and scan your files, read in the information, and build up a new index.
You can see where I'm going with this.
USE A TAGGED FILE FORMAT. DO NOT USE WAV.
I'm going to get this out of the way up front. You're desperate to start ripping, you've got a PC, Windows Media Player is already installed, so you're going to use it. DO NOT USE WMP - at least until you've understood the alternatives. For a start, WMP only supports WAV, WMA and mp3, and you will be sent to the naughty step if you rip to any of these.
The most commonly suggested ripping programs are
The first three support FLAC, iTunes does ALAC.
My personal preference is for dbPoweramp - its lookup of metadata when you insert a new CD to rip is very good, and it effectively uses "crowdsourcing", comparing your rips with those of other users to ensure they're accurate. I'm sure others will chime in with details of their favourites.
Let's face it; iPods.
iPods don't support FLAC. If you're in a homogeneous Apple world then you've ripped to ALAC, this will play in iTunes and on your iPod and all is cool.
If you have non-Apple kit, you've ripped to FLAC, which won't (without serious intervention) play on your iPod.
You'll need to transcode from FLAC to (usually) mp3. You can either maintain two libraries, one lossless, one in mp3, or some software such as MediaMonkey can transcode on the fly to synch with an iPod.
Use a lossless format.
Use a tagged format.
This leaves you with FLAC or ALAC.
Transcode to mp3 for your iPod if you're using FLAC
I rip with dbPoweramp, for reasons mentioned above.
I manage music with MediaMonkey - it makes bulk tag editing very easy, and has good transcoding abilities.
Flame on ...