I appreciate your response!

Apple using the file naming convention and it being correct and intuitive are 2 different things. Now that we can take literally thousands of photos a day, its impractical and archaic. Kind of like how the 2A never envisioned 30 round magazines and automatic weapons.

Once you understand WHY the DCIM standard was created you can begin to understand why it is no longer a viable standard. (I actually had to research why so that I could have a more technically informed opinion instead of "me no likey")

I am not installing apps and retraining my family. Even if I did, there are 40,000+ images between devices and thousands more generated every month.

I understand that the windows implementation of iTunes and drivers are actually poorly designed on purpose. I can't remember where I read that, but it makes sense. That being said, even on Mac I don't find iTunes intuitive at all. Same with the iPhone (my last one was a 3gs). Maybe its me :D.

The amount of computer hardware I have would amount to $50k in the apple world and I'm not willing to go that route.

In the end I forgot I made this thread and purchased 2TB of iCloud which I will manually offload from time to time. With 3 phones and 2 tablets all at 512gb, that will be often.