He isn't alone, though from reports I've read, it is mostly limited to users who have:
1. A number of devices with dissimilar libraries across them.
2. Large, complex music libraries.
3. Initiate the original sync from their mobile device, rather than iTunes on a Mac or Windows computer.
There's been some grumbles from press, and yes, Dalrymple will generate a response from Apple. Pretty much no one else in the press can generate a response quicker (maybe @gruber, but I'd even give The Beard the edge).
Many of the issues are that the Match doesn't work via fingerprints when initiated from an iOS device (but uses tag-matching instead). A bunch of Jim's issues fall into this category.
It is a cluster for "advanced" users, though, and it seems way too easy to accidentally get your stuff replaced with DRM copies (apparently some of this has been fixed in recent, still-beta releases). Though many, many "regular" people I've talked to have been happy with it, I think for anyone who would be interested in MC...
Stay away. It is not for those of us obsessed with our libraries.