I can imagine there frustration of such small but repeated bugs.
I think the big problem here is the tech really: re-compiling maps for such minute additions is really painful. That's also the kind of thing I would get an apprentice to do (would be cool if they hired a couple, I mean for first gig).
Something they could work on to implement is a bomb clip mesh that the 3D artist could build from the start(?).
And for stairs in Source 2 they could make a stairs tool that would save the hassle of clipping (and more annoyingly to re-clip at any change – group, ungroup, func_detail and all that mess)