That...both makes sense and is really dumb. However I'm not convinced that's the issue here, as I haven't rotated anything. I like the idea of the attacher you linked, will definitely check that out!
I would still like to better understand why this is happening though. Doing some more testing while typing this reply, the behaviour of transitions really has me shaking my head. If i attach the trans direct to the fan, then top is top. If i attach a different fitting to the fan, like a canvas or a straight, and then the trans, i get the behaviour as shown in the snip in the OP. However if i keep adding straights between the canvas and the trans, i got even more bizarre behaviour. With a canvas, a single straight and the trans on each side, i ended up with top being bottom for both trans, and then for each straight i would add between the canvas and the trans, top would flip for both of them. ie 2 straights has top as bottom, 3 straights had top as top, 4 straight had top as bottom
This is very bizarre to me and something seems very messed up about this implementation. If no one here can explain this i may report a bug.