iTunes / iCloud Error 8364

Greetings,

I have family using a desktop with iTunes, three laptops running iTunes, a pair of iPods and three iPhones. The whole family shares a library and we run iTunes Match and iCloud. Back in 2007 I did a massive project uploading my CD collection onto an external hard drive then onto iTunes. Since then I have augmented my library almost purely through iTunes purchases. I could pretty much narrow down my issues to having started when iTunes Match was launched. Songs and whole albums that I purchased through iTunes and uploaded onto my iPhone via the iCloud will refuse to play. More specifically I'll select a song from a list of songs by an artist and it will just forgo my selection and play a later track. This happens with specific songs. I found I could resolve this issue by redownloading the whole album from the "Purchased" playlist off the iTunes store. Unacceptable on Apple's end, but oh well. My newest presented problem is similar to the aforementioned except it happens off the iTunes library of my laptop. I will select a track that has been in my iTunes library for years (the amount played count is 35) and it will skip my selection. Entire albums are like this. I do not have the original CD. The track info says the album is on the Cloud, but if I try to download it I recieve error 8364. Explanations?

edit: typo on error number