Basically my problem is that I had to install 64-bit version of Chrome .deb package, which doesn't support 32 bit flash plugins. Annoying. Luckily there is a native Flash Player build that can help out, it's called Flash Player Square. Problem is, it's not very helpful on how to Install. I assume most Linux users would already know, but since I'm new to Ubuntu and Linux having a GUI then I wasn't sure what to do with the .so file. Turns out it's very simple.
All you have to do is copy libflashplayer.so file into the /usr/lib64/mozilla/plugins directory. Once you've done that simply restart chrome and visit about:plugins in your address bar and you should see Flash is enabled. Seriously, that's all you have to do. Personally, I was a bit let down because I love the challenge of hacking things and this way too simple to think possible! Looks like I'm going to have to find something else to hack to finish up my weekend; Triple Gateway Secured Proxy, Personal SVN Server and Spotify on Linux? Sounds fun..