Speaking with my usability hat on (my degree is human machine interaction) that isn't a useful question as there is one correct answer: plug whatever devices in, in whatever order and combination.
OK, you plug a power supply, two laptops, and three monitors into a USB-C hub. What happens?
Any kind of bus where peers can negotiate protocols is going to have severe usability issues. Just look at the MacBook that's plugged into itself: https://photos.app.goo.gl/G2PivEo1JrKKtA9W6
Given the fundamental usability problems of USB-C, I don't think there is anything anyone can do toward making a simple USB-C hub.
Cost to create a hub should have been a consideration of the spec designers.
I'm involved (on the very edge) of C++ standards, and we often reject proposals because it would be too hard to implement, or too hard to teach. The proposal itself would be a useful, but the costs are too high.
