Rob has an issue with iTunes for Windows. He's got iTunes Match turned on and iTunes crashes. When he disables it, everything is fine. Leo says that iTunes for Windows has never worked right. Apple just can't get it working reliably on iTunes. Leo says that there are some things to try. Uninstall both iTunes and Quicktime and reboot. Then reinstall them separately - with Quicktime first. Then install iTunes. It's been Leo's experience that cures a lot of what ails iTunes for Windows.
Then, when he runs Match, he should back up his iTunes folder, and then add to library. He should delete his iTunes folders, libraries XML files, and everything but the music. Then re-import and have it rebuild the database.