Did you know you can use the knife to guide your booleans to get them to solve better for better behavior with bevelling?
In this example I used the bool tool to cut into a cube and just used the default solution to just proceed. As you can see the corner edges provide poor guidance for the bevel that was used afterward. The narrow triangles that converge on a single point will guide the bevel in that direction causing issues. This is something best realized by experimentation but it can definitely cause some issues.
Now for my solution. Guidance edges.
On this 2nd example you can see me go in edit mode and use the knife with (K) and also (Z) to cut through and (C) to constrain and cut a line through before applying. The result was a support edge that isnt connected to the poles that are in the corners. Allowing me to get more versatility with the bevel modifier and the subsequent bevels.
So what happened here? Well the boolean has to solve and place connecting edges somewhere and the place it puts them isn’t always the best. In fact lacking these sorts of adjustments will make subsequent bevels more difficult due to trouble exponentially increasing with each poor solve. I feel this is part of why people don’t care for booleans and bevels but there is a system that gives control back to the user.
This is a behavior I take advantage of frequently to basically boolean to my advantage and get away with doing less cleanup.
I hope this tip helps and happy blending!
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From Imagination To Creation 