UPDATE - RESOLVED:
Short Version: 3rd party ribbon cable used for Duex5 was causing problems, suspect voltage drop.
Long Version:
After another couple of weeks, the issue spread to attempting to boot with USB connected as well. Connected the DuetWifi to a known good USB3 port on a windows system to update the firmware. Did so successfully, then after hitting the reset button, followed firmware instructions to a T, the DuetWifi went into a reboot cycle. It was cycling about 1 - 1.5 times per second.
After some more troubleshooting, I identified that the longer ribbon cable I used to connect my Duex5 was causing the reboot cycle in some fashion. Exact root cause is unknown at this time, I suspect drop in voltage due to cable length / gauge. Replaced cable with one that came with the Duex5 and DuetWifi immediately booted and does so evertime now. Plus I no longer need USB connected to boot and serial over USB is working again.
So the longer ribbon cable was causing nearly every issue I was having. Not sure if it's just a cheap cable, got two in a pack, both exhibit the same behavior. Regardless I am back online and letting folks know in case they run into the same issue.
Dave, not sure if you have a warning on the Duex5 page about this, but you may want to add one. Use good ribbon cables… 🙂