FYI, I just updated my Nvidia Shield TV Plex app player with the latest version (9.28.0 - Aug 1st) and the ‘Picture-in-Picture’ is working now for my OTA guide channels.
My current levels are now:
Server Version#: 1.32.5.7349 (Windows based)
Player Version#: 9.28.0.3162 w/Nvidia Shield TV (8.2.3)
Tuner Make/Model: HDHomeRun Flex4K