like paper airplanes

I have a fairly large collection (at least, big enough to feel a bit daunting to rip... again...) of CD's. These, combined with downloads free and iTunes, make for a 35.49 GB music collection (Not including my own recordings)! I currently have my CD's ripped to lossless WAV using Windows Media Player. However, I've heard FLAC is higher-quality than WAV. My experience with FLAC leads me to not be surprised, but before going and re-ripping all those CD's, I thought I'd check with MusicBanter.
My only concern here is sound quality: I want something as close as humanly (computerly?) possible to the original CD. I don't care about file size.
As a final note, everything I downloaded (barring iTunes files and some things from netlabels on the Internet Archive, which I can convert) was available in a couple of formats, including FLAC.

So my questions are:
1. Should I re-rip all my CD's to FLAC, and re-download everything else?
2. If so, what is the best software to use to rip to FLAC?
3. What's the best FLAC-playing software? I currently use Creative MediaSource 5, but I have no idea where or when I got it, and would be open to changing.
4. Is this really going to sound much better? (Yes, of course it'll be better than the mp3s, but is it better than WAV?)

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RYM