My Media Won't Play in iTunes or on my Apple TV (Except Music)

I am unable to play content in my library, whether purchased from iTunes or whether it is a media file of my own that I have added...be it purchased, obtained from a friend or stripped from a DVD using Handbrake or Wondershare Ultimate Video Converter. I am running iTunes version 11.1.3, which I am told there are no updates for.
Yesterday I purchased a season pass for Elementary Season 2. Apple happily took my $45, but none of the episodes will play.
I am running a registered copy of Windows 8 Single Language 64bit.
What is going on, this has been a problem for months now? I have seen numerous blogs about the exact same thing.
iTunes is promoted as a media player and media library application developed by Apple Inc. used to play, download, and organize digital audio and video on personal computers running the OS X and Microsoft Windows operating systems. The iTunes store is also available.
So...regardless of where my media comes from, provided that it is in the correct format, it should play.
I am honestly getting so sick of Apple. I have spent a fortune on Apple products, 2 x Apple iPhone 4's, 2 x Apple i Phone 4S, 2 x Apple iPhone 5, 2 x Apple TV's - 3rd Generation, 1 x Apple Airport Express, 1 x Apple iPad2, 1 x Apple iPad 3, 1 x Mac Mini, 1 x Apple iPod 64GB, 1 x Apple iPod 8GB.
I can't afford an Apple PC big enough to house my media library...that a dream that I'm saving for, but I have seen people running iTunes on Mac's experiencing the exact same problem. Oh, and I can't stream from the cloud, because my 4mbps connection means that I have to wait hours for a movie to play.
I choose to house my library locally on my little HP server backed up to external HDD's.
Should I abandon apple all together and switch over to a competitor?
Kind regards,
Ursula

Delete and redownload it if doing so is free in your country.
(100141)

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