I would say that the attempt to form the connection in the first place will tend to get you into trouble. Connections form - but it's almost (or entirely) a function of what you're doing inside yourself.
Yeah, it's a little bit of a head twister...
sure, with someone with skills it's very different. I had a very specific scenario playing in my head when I said that (kata otoshi), direct, irimi, , but yes, you move your connected body and the connections happen. It's always about what you're doing in you.
A head twister, to be sure, but how much more interesting is it than before?