MacPro 5.1 running Yosemite 10.10.5 and iTunes 126.96.36.199. iPad Pro, 2015 model now running 14.1.
Until the 14.1 update, the iPad was happy to transfer a folder of pictures from the Mac to the iPad via iTunes. Now, after update, iTunes gives a warning that 10.11.4 is the OS needed to let them talk. Aside from the fact that I wish I knew this prior to updating the iPad, I'd like to find a way to continue this one process.
(Note: Over the years, I've accumulated a lot of paid software, and when I loaded 10.11 to another drive to test it out, there were loads of casualties. To the point where I decided I'd keep Yosemite on my main Mac, and buy a mini when Mojave was needed, as it will be to do my taxes with TurboTax in April. The jerry-rig solution would be to use the mini to do this.)
I see software such as "Waltr" which performs such a function for audio. I'm hoping to find a method that will work for photos.
FWIW - I have math problems or images that I need to screenshot and move to the iPad into Penultimate (a sister software of Evernote). This lets me write and create an assignment I can present via Zoom or turn into a PDF post edit. The Mac screen shooting avoids the need to edit the image, VS looking at original work on the iPad and screen shooting that. The process was tedious but manageable when iTunes let me bulk transfer the images.