iTunes has several ways to select a particlar item for a device, making it easy to think you have selected it by one criterion, while you have blocked it as part of anoter category. Particularly if you think you've selected it by playlist but have deselected the album.
Another way you can miss things is to have selected "only what I've bought."
I don't think Match has to do with loading to the player. Match is about replacing what you've ripped with a copy of the same item from the store. If you are loading only what you've "Matched" then I would expect not to get what was ripped but not matched.
I think iTunes is way too complex for most people, it has been made too much of a heavy-duty management tool, and doesn't always fit the way you think of your library, so you can get messed up fighting the tool to make it do things your way rather than iTunes way. But almost all specialized data management tools have that fault, you notice it only when you have the personal mismatch with the guy who designed iit.