There's nothing wrong with your theory, except you have to know that distance. It can change depending on how the drill is ground. But it's a good approximation. You also have some small radius on the reamer that will need to be accounted for. If you were doing production work, that might arguably be the best way to set up a punch card.
Personally, if I were doing a one time thing, (and I had a DRO....), I would use the feeler gauge/drill tip/DRO zero you mentioned NOT to calculate the depth of the half inch reamed area, but to set the " safe enough to not blow through" point. How long is the workpiece? how much do you have to work with?
You didn't say, but if for example, this was a one inch long piece that's a quarter of an inch to work with. Less 0.100 for the drill tip (pencil and paper math, verify that), you'd have 0.150 inches to blowout. Which will deform the back before it blows through, you've got to leave "some" material there. Put 0.050 inches in there at minimum to ensure no marks on the back of the part. But I think you can leave 0.100 there.
My suggestion is to use the feeler gauge to find the drill tip, "find" that tip with the feeler gauge as you said, drill in 0.900 from the TIP, not the diameter, which will leave 0.800 of drilled cylindrical area. That leaves 0.050 "window" which is plenty to burn up any radius that will be on your reamer, and still leave a somewhat comfortable safety margin at the cylindrical reamed hole depth, (you can always drill deeper), and a VERY comfortable margin at the blowout point (which pretty much scraps a part).
Basically what I'm suggesting uses the same math as what you're suggesting, except I've changed the reference points so that the "subject to real world error" parts are moved to where you can recover from a little discrepancy.
For a THEORETICAL 135 degree drill point (tan22.5)X(1/2 drill diameter) will tell you how tall the theoretical point on your drill should be. If we assume the angle to be correct, then any small error from the grind (if it looks "good" at the point, that won't be much) will make the tip's actual point "shorter" than theoretical. The only way to make that point longer is to mess up on the angle of the grind.