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Comments
Alternately, you could make through holes with that sketch and then add countersinks with the selection fillet custom feature (which also can make chamfers).
I'm sure there are several other options that I’m not thinking of.
What you've suggested will work & if I'm 3D printing the parts I use similar technique (normally boolean subtract) but I like to use the automated hole callout table on my cnc'd parts so the drawings are correct. AFAIK what I've asked for in my initial mail isn't possible.
Here's a simple example: https://cad.onshape.com/documents/86cd2d6cc3e920442c7ae169/v/4fae4df79c1cd62d05e0895f/e/eaf176b233dde51a7a91e53b