I prefer to use a drill guide and a drill press. DA or PSP MFG, either one works the same. But with any drill guide I still always need to re-drill the holes a few times to get the bolts to go in smoothly...i.e. no side loading. I don't like any resistance to the bolts threading in or you're asking for them to be sheared off from side load.

I have used the prop washer to mark holes and drill on the drill press. That worked just fine. It's better to mark the holes while the prop and prop washer are on the prop shaft for better accuracy.