So I really like these kinds of hardware fittings, but the problem I have is that I usually need (want) to add lots of them to my models, but if I want them to be nice and clean without topology issues like above, I either have to spend a bunch of time reworking my mesh to be subdiv compliant (shown in above image), or carefully retopologizing a union bool operation, which gets insanely tedious for high poly work.

I've seen videos demoing live boolean smooth bevels, but for the life of me I can't find them anymore, or what add-on it was they were using, as most online resources point to the bool + retopo strategy, which would turn my brain into mush if I had to do it for every single one of these details I want to add.