No, I didn't go back to the original CD. I can see your point that I actually got lower quality song this way. The fact however is that I got better matches, but perhaps you're right and it's a matter of 'chance' that they now matched. At least this confirms that the matching process is fuzzy.
I don't think anyone questions that the matching procees is not going to give you exactly the same results every time. Outside of Apple, no one knows exactly how matching is done, but it's generally accepted that some form of waveform matching is used for part of it. Whether they look at exactly the same segment of each song every time isn't known. What the allowable deviation from a "perfect match" is isn't known, etc. It is generally believed though that the better your original copy, the greater liklihood that it will match. Garbage in - garbage out as the saying goes.
But, if you're right then the solution to get a 100% match would be to try and rematch the song over and over again until it matches. However, there is no re-match option in iTunes. Which would mean backing up the song, removing it from iTunes and from the cloud (therefore loosing the metadata) and re-add it again. Sounds like a dreadful process. Unless anyone has a better idea?
If someone wanted to just spend all their waking hours trying to get re-matches simply by re-submitting I imagine they would have some success, but it would probably be a situation where diminishing returns made them give up pretty quickly. First, while it's been discussed on the board many times, no matter how certain a person is that their personal copy of a song is identical to what is for sale in the iTunes store, they could well be wrong and might never find any information that will tell them they're barking up the wrong tree. Second, if as I mentioned earlier, what they are submitting has been so compressed that the matching process can't recognize it, you could bang your head against the same wall time after time. Personally, that seems like an incredible waste of effort.
The "better idea" you are looking for, well the best I can suggest is that if you feel the percentage of matches you are getting is unacceptable, contact Apple and tell them. If part of your concern is that many albums have almost all but a few tracks match, tell them that too. I'm one who is willing to be patient. it's not that important to me whether a track or two doesn't match, but then I ripped all of my CDs directly into iTunes as 256 AAC, so I'm really not missing much there. On the flip side though, I'm happy to see so much of my vinyl matching. I didn't hold much hope than it would and I've been pleasantly surprised.