Thanks everyone for your insights. I really appreciate it. I took what everyone offered and, just like when I was a programmer, I dreamt the entire night about doing this work. So, this morning, I made a simple jig using double stick tape and two rails with 60 degree edges. I clamped them to the cylinder and used my hand drill to drill all the aligned holes. Here are some photos of the outcome. Again, thank you everyone.
Front view of the jig setup. The rails will support the drill bit
Rearward view showing the use of the double stick tape
Dilling completed
Completed piece with the rails in place. I made another quick jig to drill the 3/16" rail inserts with the 3/32" hole for the hand rails. For those of you who have already build the T&J Olde 99 Locomotive, it's about 1/2 way complete with only straight forward work left.