I dumped 20GB of MP3s onto iTunes (for Windows) and had the application churn for a while, then crash - repeatedly. However, I've since switched to Winamp5 and have no intention of changing to anything else - so I don't know if that was just an older version issue.
The issue with Winamp that will make it take forever is if you set "Read song information when loaded into Winamp" - because then it'll go touch every MP3 and read the ID3 information out of it. Just change that to "on display in playlist editor" or "on play", and you'll be fine, no matter how much you toss at it.
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