I have 2 Squeezebox3s and I love them! I do not use my CD player anymore. It is just so convienent to have my entire library at my finger tips without searching for CDs. I actually listen to a more music and with more variety because I do not have to find CDs anymore. Oh, and it sounds great too! This put the final nail in the coffin of my surround sound/hi-res experimentations and honestly I couldn't be happier. Less cost and less frustration.
The only problem is that there is a bit of a learning curve. You will have to learn a bit about tagging, ripping software, the SlimServer software, and music management software.
I use Foobar2000 for tagging, transcoding when necessary, and for music management. But, Media Monkey is better for newbies and you can also auto-tag your music from amazon.com. Both are free.
I use EAC for ripping and it is the best but not the fastest and that is because it makes mulitple passes to ensure data integrity. It will take some setting up. You will have to download 3rd party encoders and point EAC it to your these encoders. I control EAC using REACT which is just a configuration script that allows you to have multiple encoders and settings that you can use with EAC. It makes configuration changes to EAC a lot easier. I recommend LAME 3.97 for mp3 encoding and FLAC for lossless encoding. Again all of this is free.
Or you could just use iTunes for everything and point the SlimeServer to your iTunes music library. This is dirt simple but I do not use iTunes because it does not support FLAC nor does it use LAME (which is the best) for mp3 encoding and I do not like Apple's monopolistic business practices.
Avoid Microsoft because their music management software (Media Player 10 and earlier) is a steaming pile of confusion. It is no wonder Plays for Sure is getting beat in the marketplace.
Lastly the supplied remote isn't that great but my opinion is that you just can't lose with a Squeezebox.