I started shingling the roof yesterday. I attached a 2x6 to the eave with 2x4 spacers using timber lock screws. This enabled me to attach the drip edge and rest the ladders against the 2x6 without destroying the drip edge. The hardest part was laying the tar paper. The paper has guidelines on it and I had to get them level so my shingles would be straight. Attaching the shingles was straightforward, I just had to cut the shingles along the edge to get the proper spacing.
This picture shows the drip edge with the ladder resting on the 2x6. Just above the 2x6 on the right side is a section of 2x4 spacer. The 2x6 was also useful to rest shingles on, so they didn't slide off the roof.
This is a view from the end. You can see the 2x6 and sort of see the 2x4 spacer.
Here is the first side of the roof, almost finished.
My feet are tired from standing on the ladders and my thighs are sore from leaning against the ladder rungs.
I'm thinking how to set up my ladder to work on the last row of shingles up near the peak, considering how I'm not fond of heights. My thought now is to attach the ladder stabilizer to the top of the ladder and lay it parallel to the roof. The stabilizer has rubber feet which reduce movement. I would secure the bottom of the ladder with a line so it doesn't move. That way I can stay on the ladder as I put the shingles on at the peak. I can also lean over and apply the top row of shingles on the opposite side.