After monkey-hacking the PL2023TA from a reddit post, I was able to successfully use my UV-82 image to upload to my new UV-16. I am using a legacy Baofeng brand programming cable and did not want to wait for a new Wimpdoze 11 cable when I have a new radio sitting here begging to be programmed.
Backstory done: I was able to upload my existing image without too much fanfare, though it requires two attempts to connect everytime I upload or download the unit.
That being said, I used the BF-F8HP as listed above, but my PC/cable combo used com6 channel instead com1 channel. On newer PCs, the channel can vary by which USB port used, etc.
You might download the chip check tool if you are using the PL/Prolific series of cables. It will verify what com channel you have been assigned. I originally knew where to look by digging into the Device Manager and checking the port assignment.
I am somewhat miffed that the unit includes a USB-C port for charging but is not usable for programming. What an oversight!!!
I hope this helps someone else not spend multiple hours trying to route around the mulberry bush to get their radios radioing.