A handmade home for woodworkers and admirers of woodworkers. Our community icon is a planter box made by @Captain Aggravated, the winner of our summer '24 woodworking contest. Congratulations!
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.
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)
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.
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
I have this exact tool, and just as a warning, it is far from perfect but it does certainly help and I've used it for many things but if precision is what you're looking for you might be better off buying a higher quality one or a chuck and building one at the angle you need.
Milescraft makes a slightly better one and then there's the rockler one but you know, you get what you pay for.
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.
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.