Can you drill a thick ish square of wood in the drill press and then use that as a guide for the big piece? (Clamping it down). That's about what I would do. (I might use a metal insert on the guide if it's super super critical)
Note: I'm Not an experienced woodworker, I've used this before for drilling 3d printed pieces.
Yes, making a jig is the way.
I mostly work with metal, but this is exactly what I'd do OP. If it's not an option, then there are jigs you can buy that will work.
This type of guide would wear out too fast, I think. It would also take away from the drill length, which I need to drill relatively deep holes (high depth to Diameter ratio).
Then you likely want a hard drill bushing. That'll let it be thinner than a wood jig, but still tool steel to not wear out. (Wood to support the bushing)
They're a bit pricey, but if I understand your situation correctly, a drill guide sounds like the thing you're looking for. I think you can get something decent for like $50. And of course, if you want to get stupid, you can spend as much as several hundred
I think that's exactly what I need! At least this type of drill guide:
Why are very different kinds of tools named the same?
I commented further up, I guess I should have scrolled first. This is exactly the kind of store bought jig I meant; it should be exactly what you need, as long as the base isn't too big for wherever you need to drill.
The really cheap (Princess Auto, <$20) ones are alright but not great, the more expensive ones are fantastic
My suggestion would be to use a plunge router to create a 2 - 3" deep hole (not sure how deep you need to go) then follow up with a drill bit in a hand drill to finished depth. The routed hole will keep your drill square.
How precise does the angle need to be? I can usually get really good precision for a couple cuts by just using 90 degree reference surfaces on two sides of the bit. So either an inner 90 corner or 2 gauges setup tangential to each other. That may not give enough precision for what you need though.
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