Well, I appreciate the mental exercises you're putting yourself through. The questions are interesting. Still, at the end of the day everyone's process is a bit different. Since arts and crafts are subjective, quantifying how those two things merge is only useful up to a point, imo. And, of course, that point is usually wildly different for all of us doing this stuff.
I'd ask, do you really wanna chase what that means? It might always be ephemeral as context changes; slipping out of reach. And shouldn't such meaning remain in the realm of intuition anyway?
Then again, maybe not. At least not for everybody.
Perhaps being in a space without firm answers isn't interesting to you? Maybe striving for technical contentment at the limits of understanding is the thing you enjoy. That's cool too. Engineering can be artful in it's own way as well.
Either way, keep poking around.