Seriously, I’m asking. I don’t know because I have more than 25,000 non-iTunes songs.
iTunes Match is a feature of the new iCloud that will scan your music library and match songs you own (but didn’t buy from iTunes) to songs in the iTunes catalog. Any unmatched songs will be uploaded to the cloud. This allows you to download any song you own (or otherwise acquired, cough) to all of your iOS devices directly from iTunes, even if you didn’t buy it there originally.
As it turns out, however, there is a strict 25,000 song limit (not including purchased music). I’d like to know what happens if you scan your music library with under 25,000 songs, and then go over the limit by adding more music. Currently, it appears that one would have to stop using iTunes Match.
My suggestion, as usual, is to throw money at the problem. If $25 a year gets you 25,000 songs, how about $50 a year for 50,000 songs? $100 a year for 100,000 songs. You get the idea. Basically $1 per 1,000 songs, per year. I hope that Apple will consider this when iTunes Match exits the beta stage.