Adam has destroyed his first countersink. He has a talent there I think. I neglected to get a picture. Two more 120's on order.
Here is my technique to not screw up the hockey stick again. Thought I would share it. I took a piece of 1/8" scrap and transferred the holes from the upper angle. You can see the scrap clecoed on:
To upsize to the next hole, I use the drill press to put a straight hole through the scrap and the angle:
I am only doing two holes at a time, one per hockey stick. Now the whole thing is clecoed in. I have 1/4" that I can insert the snake drill into before I drill anything. This ensures the bit is straight. Also if the hole gets screwed up, it is usually on the entry and that part is scrap:
I plan to do this with the 7/8" square angle reinforcements too. Instead of using scrap the pilot drilled blocks will get the drill going straight. Between that, the angle, and the shim it is 1.125" of depth that will be done on the drill press