I know this is an old thread, but I was going to say this is what I do to force them to "re-match." But it doesn't always work.
What has helped is....I bring up on the web the song and album in iTunes (search "Abbey Road, iTunes"), and then peruse the details of the song and album to see if anything is off from the version you have. If I have tried to create new AAC several times and it's still not working, then I'll even work on the song length if it's a bit different. Say a song in iTunes is 3:35, but the version in my catalogue is 3:38, then I can go in and figure out where to cut it down. Usually maybe start it at 1 second instead of 0, then end it at 3:36 instead of letting it run out. Next create new AAC version, and your new version will be 3:35. This is also a good method if you somehow get a disc that has no breaks between songs. It's tedious and time consuming, but you can manually create each song. (If you ever need to do this, I recommend pulling up a time calculator app online, some even will let you add multiple items; in which case I'll add each songs length one after another, then I know where in the whole 1 hour and 12 minutes of tape, each song begins and ends).
Sometimes I've learned that I have the option of either having it match in iTunes, or keeping it with the metadata of the original disc. I am picky, and prefer to have all my songs tagged with the original song data, instead of being tagged in a Greatest Hits, or "Hits of the 90's," etc. But with one-hit wonders and others, iTunes may keep them tagged in their system related to the GH or Compilation version. So pick your poison, accurate, original tagging? Or match?