So pretty much what the title states, I already have all my splits setup, the ASL files loaded into livesplit, and the timer still isn't starting. I also have it running as admin. I have no clue what to do next.

Start LiveSplit and rightclick it, then choose Edit Splits... Search Wizard of Legend in Game Name:. Once chosen, there is an option to activate the autosplitter. Enable it and click on the tab Game Time and enter 10 splits (one for each floor / council member). Once done close Edit Splits... and rightclick LiveSplit again, go to Compare Against > Game Time. Also make sure you DON'T have the Clarity mod installed since it will not work with it.

Now when you start the game and enter a dungeon LiveSplit should work. If there are still problems feel free to ask.

So apparently it was the Clarity mod that was preventing the timer to start. Thanks for the assistance!