I keep getting this 250 items thing whenever I purchase a song.

I'm actually writing this from a separate account since the current one I use is my mom's. Anyways, I have 699 purchased songs and whenever I goo to the Purchased list on the iTunes store (not on the player btw), it says I have 250 items. Whenever I buy another song, it still says I have 250 items. What does it mean? Will those other songs be taken off if I upgrade to a new computer?

If you mean the Purchased link under Quick Links then the 'recent purchases' list on there only (I think) shows the last 250 songs that you bought. The list of artists on the left-hand side of that screen should let you see your older purchases - or go into Edit > Preferences, and on the Store tab on there tick the 'show iTunes in the cloud purchases' tickbox, and they should (if not already downloaded) then show in the Music part of your library with a cloud icon against them for redownloading.
Changing to a different computer will not remove items from your purchase history, but songs (and any other purchase) could be removed from a country's store by the rights-holder at any time - you shouldn't rely on being able to redownload any item, you should be keeping and maintaining a backup copy of all of your downloads.

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