Boring Angles for Chair Leg Mortises
For hundreds of chairs, there are machines available to do this, but I'm guessing you are not looking in that direction.
From contributor A:
I used to have a chair factory, completely vertical integrated from the dried wood up. We made our own scoop seats, pressed chair backs, bent chair bows, turnings. Didn't make dowels - too cheap to buy them.
We built 120 chairs per day for many years. What we used for leg screws was to lay a drill down at a fairly low angle, and drill a 3/16" hole in each leg. Do this from inside the leg area, harder to do but less visible. Then put an inch and five eighths wood screw in each leg.
That and the glue will hold the legs in just fine. I still have a set of those chairs, going on twenty years and they are still holding up great.
From contributor W:
Get one of the books on Windsor chairmaking or Shaker chairmaking. Or take a class from Brian Boggs or Mike Dunbar or Curtis Buchanan. Adapt their handtool techniques to your drill press. Well made Windsors and Shakers will last a few lifetimes. I use a compound 5 degree/5 degree that gives a very stable chair. However I don't use a plank seat.
From contributor E:
You really must make up a jig with the correct bored hole compound angle. If you don't, your chair is likely to look wonky. I suggest a wooden block about 3 inches thick that could be clamped to the seat of the chair.
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