In regards to the problem above ^^
Turns out it was my server causing the problem.
I was serving the video using php's built in server which doesn't cut the file into chunks (at least not straight out of the box).
If anyone has a similar problem, this link should help http://stackoverflow.com/questions/8088364/html5-video-will-not-loop
Even though it's talking about looping a video, it still answers the question.
I fixed the problem by setting up a virtual machine with vagrant but that's probably too advanced for the average user. If you're having trouble, try using "wamp" or "xampp".
Long story short, you need a server that can send a video in small chunks.
Hopefully this helps people out with similar video playback problems!