All 226 Beatles songs from the 2009 remasters matched for me. It's the one full discography that I not only own, but attempted in iTM. SCITTBW, from my testing, is problematic on the original 80's CD only (I tested that as well). As for DSOTM, how many times has that been remastered? This is one of those albums that seems to get the remaster treatment every few years, so it doesn't surprise me that it would not match most of the time.
As for the adverts, of course it's going to be deceptive - it's an advertisement. I've actually read them over and it says "most of" or "probably", so there's that wiggle room in case someone complains. But I agree with you that masterings are never brought up and perhaps it should be (even as a footnote at the bottom - something like "there is no guarantee that your albums will match due to masterings, bitrate or other factors out of our control"). But I only can't see how having multiple masterings of these albums in the Cloud are going to be feasible for them - it may not even be allowed by the labels.
I've actuallly done some more tests with my own CD rips, and the general pattern I've seen so far is that music from the last decade or so, in general, matches quite well. But CD's from the 80's or early 90's have a significantly lower chance of matching - sometimes it's OOP so it would upload 100%, or there was one or more remasters where one or more tracks don't match anymore. But I still get a few recent CD's that have that one elusive uploaded track that makes no sense at all.