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Making Winamp your default player is simple enough. I'm using Winamp 5, so if you have 2 or 3 it may not be identical, but I found a menu under General Preferences called File Types. You'll find a list of supported extensions and you can highlight the ones you want to use Winamp for, or use the 'All,' 'Audio Only,' 'Video Only,' or 'None' buttons to select the appropriate files.
As to the other, I can't really say for sure, since I don't know what file type MusicMatch uses. If it's an mpeg or ogg format (including mp3 or mp4) Winamp will have native support, but if it's some crazy proprietary thing you might need to re-encode the files. This can usually be accomplished by converting them back to .wav and then grabbing an encoder to re-compress them in the format of your choice.
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I wake up in the morning more tired than before I slept
I get through cryin' and I'm sadder than before I wept
I get through thinkin' now, and the thoughts have left my head
I get through speakin' and I can't remember, not a word that I said
- Ben Harper, Show Me A Little Shame
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