Thanks again for all the comments - here is where I've ended up:
-Drill from backside (using TSC drill)
-Chamfer (ends up being exit side)
-Flip
-Chamfer entrance and some other features.
-Tap (form tap in this case).
My logic (and I'm definitely listening to those with more experience that I have)
-I want this to run without tool breaks - right now, it's 1 up, but I'll have 6up on the next fixture.
-TSC drill since I'd already bought it, and no issue with 1 plunge.
-Form tap to eliminate chance of chips jamming the tap and breaking it. Seems to work well so far.
Right now, cycle time is loooong - about 45 minutes. I'm tapping at 300rpm, so will look at increasing this. My machine runs in position mode up to 1000 rpm, but I'll ease into it.
I'm happy with the quality with some tweaks to the chamfer depth. No hand work needed.