For reference, is case someone runs across something similar:
We went back through things with a fine toothed comb, we were able to get the new boards to boot a few days ago.  Our bench tester power up sequence had changed (thought the board with the OSD3358-512M-BSM powered up with the same sequencing as always).  An external +3.3V to +5.0V level converter tied to UART1 and UART4 (on a USB-to-Serial convertor connected to the Test Laptop) was powering up after SYS_3V3B, where before it was first. It is totally unclear why the UART IO pins being unknown would affect the boot up process, but we are up and running.
I would note, I found some SD images would complete U-Boot and others would not. This could be just timing, or U-Boot may be sensitive to data in the other UARTs.
In summary: Always verify all IO are in a known state at boot time if you are having odd boot issues.
After re-walking the PocketBeagle and our board schematics for the up-teenth time, we found the SYSBOOT pullup rail had been tied to our board’s common 3.3V rail, not the OSM3358-SM SYS_VDD1_3P3V rail. We verified on the scope that the 3.3V rail powers up much later than the +5V used for VIN_AC. I checked the power rail sequence and current requirements and added a jumper tying the SYSBOOT pullups to SYS_VDD2_3P3V (we don’t have access to SYS_VDD1_3P3V). The device boots properly now.
I would be interested in a reference design covering the addition of Wifi and Bluetooth connectivity. It appears TI makes a line of modules that mate to the AM3358.  It is possible to dig through other BeagleBoard designs, but a clear reference of the suggested minimum pinout connections and Yocto image tweaks would be great.
Octavo Systems LLC all rights reserved
OCTAVO is registered in the U.S. Patent and Trademark Office. OSD, C-SiP, and the Octavo Logo are trademarks of Octavo Systems LLC.
"*" indicates required fields
"*" indicates required fields
"*" indicates required fields
"*" indicates required fields