I have long considered using iTunes Match, but am hesitant because frankly I expect it to exacerbate, not solve, this problem. I ripped my CDs manually and this never, ever happens with those; it's an issue exclusive to iTunes purchases -- on which it occurs randomly and without identifiable consistencies.
Bearing in mind that this is a widespread problem, I'll give you just two examples: Madonna's MDNA album, purchased in its entirety, synced fine for a couple of years. Out of nowhere, iTunes extracted the album's lead single, "Give Me All Your Luvin," with its single-release as the album title, separating it from the rest of the tracks -- which of course I didn't notice until listening to the album and finding the track getting skipped. Because it was now listed as part of a separate album.
The most recent, even weirder, example: I purchased Rihanna's album LOUD on iTunes in 2010. Again, no issues -- for years. Just yesterday, out of nowhere, I find the single (not even the lead single on that one) "What's My Name" listed as a separate album, with its "single" release as the album title. What the ****?
The other reason I resist iTunes Match is because I also have purchased bonus or separate tracks to other albums, then manually gave them the "sort by" album name of the full album so they will be grouped together. A few extra tracks on Lily Allen's "It's Not Me, It's You" album, for instance. I used to be able to do this easily and with no problems. But over and over, iTunes re-separates them with their own track titles as the album name, separating them in my iPod. I fix them again; iTunes separates them again. Over and over. This issue made slightly more sense since these particular tracks were not originally part of the full album tracklist and I manually changed them. But this was not the case with albums like MDNA and LOUD; iTunes is starting now to separate tracks willy nilly from albums that should always have been complete, grouped track lists to full albums to begin with. I really don't get it.