Hey @RobertCNelson, the 2022-04-01 IOT Snapshot with the kernel rolled back to 4.19.x did indeed work! It boots reliably and was much easier to get the HostAPD with DHCP up and running as you recommended. I only have one outstanding issue, the kernel is kicking out a ton of this repeating message:
May 16 21:52:24 <HOSTNAME> kernel: configfs-gadget gadget: Wrong NDP SIGN
May 16 21:52:24 <HOSTNAME> kernel: configfs-gadget gadget: Wrong NDP SIGN
May 16 21:52:25 <HOSTNAME> kernel: configfs-gadget gadget: Wrong NDP SIGN
May 16 21:52:25 <HOSTNAME> kernel: configfs-gadget gadget: Wrong NDP SIGN
May 16 21:52:25 <HOSTNAME> kernel: configfs-gadget gadget: Wrong NDP SIGN
May 16 21:52:25 <HOSTNAME> kernel: configfs-gadget gadget: Wrong NDP SIGN
Note: I replaced my real hostname with <HOSTNAME>
It looks like this was an issue in the past. I am connected to a Windows 11 system.