So, I have tried using video.js and jwplayer. I've finally narrowed why they don't work on iOS devices down.
It would seem any video I upload via WordPress and then use, simply doesn't work. It'll will load forever or it will throw an error similar to the following; "“This video could not be loaded either because the server or network failed or because the format is not supported.”
It is ONLY on movies that I upload. If they aren't hosted locally, they work fine.
Anyone ever seen this issue?
BTW, I'm hosting this internally on an Apache server.