iTunes Importing?

FLAC, AIFF, and WMA are all Lossless formats and are recommended. Yes you can use lossless on large HD.
For 300 Cd's you will need approximately 120 GB for FLAC or WMA; and 240 GB for AIFF or WAV.
I use FLAC for its quality and because it is about half the size of AIFF. FLAC don't work with itunes. AIFF does, but I do not recommend it for ipod because of a very large file size.

Knownothing, You can't copy or convert songs from iTunes music store because the tracks are protected by a Digital Rights Management (DRM) scheme called FairPlay. Apple has chosen not to license the ability to play its FairPlay tracks to anyone, there is nothing we can do about it, but..... You can 'burn' the music to a CD and then 'rip' it back to your computer. This will remove the DRM protection, it will also remove information such as: artist name, track, etc, so you will manually have to re-tag the music. This is the only way as far as I know. If someone knows any other way (easier) I will be also interested. It is one of my only complains with iTunes beside price of songs/albums.

The best downloads, and my personal favorite for quality is MusicGiants and no copy protection. Second, is IMusic.com but selection is very limited. I am not 100% positive but I think it is also copy protection free . As of DRM- free Itunes the word is that they may indeed provide DRM-free downloads but for their lower resolution offerings since new higher resolution format for Itunes is around the corner. So far there is very limited library of H-resolution downloads from Itunes but I am sure it is not going to take long to rebuild their whole library around new format.
P.S
I have my own way of copying Cd and downloads that provide the best quality and convenience . Converting, copying and archiving is done by a professional company for a very reasonable amount of money ( a little over a dollar per CD or CDR ). This is my own personal way of storing my most important and best recordings.

I can give you a link if you want to try it. They can convert to any format you want.

For anyone interested in converting their most valuable collection to almost any format.
This is a link:
http://www.awaken.com
So far this is the best and one of the less expensive places I could find for conversions. Excellent customer service.
Price is about $135 for a 100 CDs, but if you have less then that it is not a problem. More CD you send bigger discount you get. They don't do DVD- Hollywood movies, DVD-Audio or SACD's. They can convert your library to CD R, DVD R, Ipod or Hard drive .

Happy Listening,
Mariusz Stark