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Welcome back from your mission, let me give you some answers/insight to your queries:
1. EAC is the best ripper because it is the only one that will make sure to do an exact bit-for-bit copy, and not skip over any unreadable sections on an audio cd. When combined with LAME using VBR, they make the best sounding mp3s.
2. Winamp definately still has a strong following, it just lost a little popularity after Justin sold Nullsoft to AOL Timewarner, who just recently announced that they will no longer be making updates of winamp 5. Yes, winamp 3 bombed, it was very bad. There was no verison 4, they combined the beloved winamp 2, plus the new features of winamp 3, to make winamp 5.
3. While mp3 is still the most popular format, there are many new rivals, and ones in particular that are gaining attention are ones that claim no loss of quality, such as the FLAC. I have not really delt with WMA, so I don't really have any insight to give there.
4. About tags, if you have a large collection of songs, I defintetly think it is worth keeping your tags in order. My view is that its a lot easier to organize them when you get them, then have to sit there and scroll endlessly through windows explorer until you find the song you're looking for. I use Tag&Rename to organize and tag my mp3s, and it works great. I have heard a lot of people having trouble with tags that have Japanese characters in them, but again I don't have any so can't help ya there.
Hope I gave some helpful info, these are just my feelings on the subjects.
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