I believe your observations are correct. Note that most people having low sussess rates are those that converted their own CDs and those with a lot of tracks that were not purchased from iTunes. Both kinds may differ in length from similar iTunes tracks (even if they are from the same album) or might be from different issues of the same album.
I believe Apple set the threshold for matching very high, and rightly so. I, for one, would be very upset if iTunes Match ignored differences in album issues (some differ radically), remastered issues, track versions from album, singles and EP versions, collections, remixes, etc. Just think how many different live versions some artists have issued. You certainly wouldn't want iTunes Match to substitute your favorite version for another live recording. I'm sure refinements to the matching algorithm are coming, but they should remain at a high threshold.
Regarding artwork for unmatched songs, Apple has two sources for artwork. Its own database of tracks for sale, and when that fails, the Gracenote music database service (which has a much lower matching threshold and is often wrong).
A user at MacRumoprs (yeah, I know...) posted a collection of observations that might be informative: http://forums.macrumors.com/showpost.php?p=13850490&postcount=58 One is that the original estimate of matched/uploaded songs is not the final one, until all three steps of the process are finished.
You might also check this thread: https://discussions.apple.com/thread/3493002?answerId=16731714022#16731714022