Advice re: capacitor placement

Not sure what you mean but it looks that you thing that GND connection with tracks is better than with filled zone.
If you really think like that (I’m really not sure) than it is wrong. You should use continuous plane to connect GND. Some time ago I have given an example of 2 layer PCB designed with whole bottom layer being GND (all vias you see there are GND vias):

If you want to learn about good PCB design you can read articles I have linked in past:

I just noticed that that thread was about Decoupling capacitors so you can also read it in whole.

I’ve never seen two ICs being connected to one USB socket. If such connection is suggested in datasheet than probably everything is ok, but I am surprised.