Sawtooth and 10.1 Combo Update Stuck rebooting

I decided to wipe the Sawtooth and install 10.1. Why? I still have no clue. I'm weird.

Anyway, I installed 10.1 and grabbed the 10.1.5 Combo Updater from Apple. I tired to install it, no dice. The Installer app was out of date (an error I had never seen before). Read further into it, Apple said to upgrade from 10.1 directly to 10.1.5, I would need to install a security update. Installed that, and boom I could install 10.1.5.

So after letting it do its thing, I clicked reboot and it took me to the blue screen you get before the screen goes black (background apps terminating). Well, its been stuck there for about 10 minutes. This is the second time I tried it. Same thing.

To make it worse, the computer tries to go asleep while shutting down, so I get all excited and once I hit a key, it wakes up and goes back to where it was. :-/

Any ideas why its getting stuck on the Combo Update reboot? Should I just go one step at a time? (10.1 to 10.1.1, 10.1.1 to 10.1.2, etc)