OK, I finally cut all but one of my holes in my pots this weekend and during the snow storm. My observations are the following:
1) Using my drill press for all of the holes made it super easy to get the pilot holes going. If you don't have a drill press, buy one on craigslist or something. you will love it. I just had to put a 2x4 into the pot for the holes near the top of the pot lip so the pot didn't bend when trying to drill the holes.
2) I drilled around 1/8" or a little less hole first and then went up a little bigger and finally to 3/8"
3) I tried doing 1/2" pilot holes with my titanium dewalt bits, and they don't work well at all. they won't go through all of the way and jam up. I had to dremel out the hole to get it big enough to do the punches, or you could just use a smaller hole punch first.
4) I tried using my Greenlee 1-1/4" and 13/16" punches with a 3/8" hole (slightly enlarged with a dremel) and found that i messed up the threads a little bit so don't do that. They recommend a minimum 1/2" pilot hole, and that is what works best.
4) I tried using my 9/16" hole punch in the 3/8" pilot hole and it worked perfectly. They recommend a minimum 3/8" pilot hole for that punch. If you then use your larger hole punches in the hole produced by the 9/16" hole punch, you will have effortless holes.
5) If you use a step bit, you will probably be able to position the holes exactly where you want. using a drill press and separate drill bits, I wasn't able to get the holes perfect, but they are perfectly adequate.
6) You might not be able to get the holes perfectly aligned using the 9/16" hole punch first, but you will not screw up your hole punches at all. If you draw a bit "X" you can use that to align the hole punches from the outside when you make the holes and get closer to perfect (when you have a larger pilot hole.)
It was overall a lot easier than I thought. The hardest part was cleaning out all of the cutting oil and metal chips from the pots after the cutting. I took a couple showers with my pots to do that, oh la la.