It had been getting a bit harder to start but it started great the day before and nothing seemed out of the ordinary when I shut it off last. The valves have never been touched in the last 200,000 kms I've put on the motor. It's definitely getting fuel because I disconnected one of the return lines between the injectors and fuel shot out while I was cranking it and there are no air bubbles in the clear fuel line. I'm going to double check the timing too, but I'm sure it wasn't pressurizing the coolant that badly before so it must be the head gasket.
Update: I tried to start it again today and still not even a kick so I figured I'd check the timing. Popped the covers off and everything seemed to be lined up, except the pump looked to be out a bit so I pulled the belt off and started from scratch. Lined everything up the best I could but the pump still seemed to be out. If I moved it back a tooth it was WAY out so I put it back where it was. Put it back together and tried it and it kicked!. Cranked it a bit more and it fired right up! I'm not really sure what was going on. I've shut it down and started it back up several times and it fires right up. It's been idling for the last half hour to see if it's going to heat up but it hasn't so far. I really need a dial indicator though so I can get the timing dead on instead of just close. Regardless, I'm parking it and putting the GLI back on the road on Monday.