iTunes is easy to use, but it's not perfect. ID3 tag and album art data isn't always well embedded, allowing other apps (if you choose to use them) to destroy tag data, or it sometimes doesn't display at all on non-Apple devices. Arguably, the resultant sound quality of the files you rip could be better when done using other applications (I like rips done with Nero in general, and actually prefer the SQ of WMA Lossless files done with WMP11 over WAV rips done in iTunes).
A LOT depends on your choice of portable player. iTunes--without using some geeky workarounds--is only designed for iPods. Lossless WAV files aren't supported on a number of devices, including the Zune HD. Zunes only work with their own Zune software. iPods in the opinions of many, including myself, aren't the best-sounding devices on the market. And so on.
I like MediaMonkey as my library manager of choice, but it can be rather fussy, geek-laden and overly technical with its UI. Rips generally sound good, and although data editing isn't as clean as it is in iTunes, it's not horrible, though the learning curve is steeper. Plus the resultant embedded metadata doesn't seem to break nearly as much as iTunes files do when read by other devices (like Sony Walkman, Zunes, Sansa or Creative Zens).
Okay I am about to start converting my CD library for the very first time. I do not use anything to play my files except Windows Media Player on my PC.
I've heard Apple's iTunes is the best music interface (on the computer).
Now first and foremost I am starting my library and down the road will purchase a portable MP3 player.
I've been using an older Roxio Easy Media Creator 7 BASIC to do some ripping to .WAV files. You should know I'm a bit of a sound quality snob so I have ripped some of my music to .WAV and then converted a few things to 192kbps MP3s.
This year I may explore a couple music paid account streaming-services such as MOG, SPOTIFY, ZUNE PASS, SLACKER.
I've used Slacker on and off and like it.
So if you were starting from scratch and did not own _ANY_ DRM-ed AAC audio files what software library player (on the desktop PC) would you use?