I'm not 100% clear on what exactly you're doing, but simply here to offer a really good File management app for the iPhone I've used for a few years.
I record on two Macs and like to transfer the GarageBand .mp3s to my phone and tablet to play in the car. Thanks to Apple's bizarre lockdown strategy with all music files, I loathe iTunes and refuse to use it.
"FileBrower" does a great job finding my files on the Mini desktop and copying them to it's own FileBrowser folder on my phone and tablet. It's unable to access the iTunes directory but you can access all your pics in Photo as well as every other non-iTunes file.
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Larrivee OO-05, OOV-03, OO-44R & Strat
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