As the title states, my library is a bit screwed up. For example, when I shuffle my entire library it tends to play some of the albums in its entirety. But this only happens to a few of them. In this case, it's Land of Pleasure & Caress Your Soul by Sticky Fingers and Man on the Moon II: The Legend of Mr. Rager by Kid Cudi. And no matter how many times I keep reshuffling the library, it tends to repeat the whole album everytime it gets to one of the songs. It doesn't even start from the middle, it always begins from the start till the end of the album.
It does this because of some broken code in the most recent releases of iTunes. They added a new feature to help those of us who want to properly group, and play in order, classical music. If the Work tag is populated then once itunes sees something in that tag it plays all of the items on the album with the same Work tag. Many have used the groupings field in the past and the latest version grabs the groupings info and stuffs it into the new Work field. So if perhaps you had something like SONY (an album label) in the groupings filed now iTunes thinks every track on the album is part of a classical Work called Sony and that you will want to hear the album in order as you would if it were movements of a classical work. Very frustrating and foolish error on their part. One hopes the can fix this in the next release as it makes shuffle play pretty much un-usable if one uses the grouping field as it was originally intended - to group songs in some way like as Jazz.Standards or World.Music, etc.