Today I reamed the brackets for the aileron hinges to final size, temporarily assembled the aileron, then started drilling the aileron countersink.
On any holes 3/16 or larger I drill just undersize then use a reamer to get the final size. This gives a much more high quality hole than a drill bit.
Drilling the aileron counterweight also went well. The counterweight is a steel pipe and it seems like a lot of people have trouble drilling it through the aluminum skin. I used a drill guide, a new drill bit and a lot of Boelube. It took some time but the 7 holes I did tonight turned out well.