This used to work but it's been a while since I had both connected. I can connect to each one separately, and they each have a different IP address.
One issue I've noticed is the iSerialNumber on the second device I plug in shows an error in USB Device Viewer from the windows SDK:
"iSerialNumber: 0x03
!ERROR: No String Descriptor for index 3!".
The first one shows "bela". From what I understand the value should be unique or it can cause issues. Can I change what the bela/pocketbeagle returns when USB is enumerated?