Using Outlook for Android in business environments for email and scheduling
I found the solution, at least on my Galaxy S8.
I have two different email apps, one for Outlook and one for Yahoo. The Yahoo one is the default email app that comes with the phone and you assign email addresses to it. From my Gallery, I select all the images I want and then share them to the Yahoo email app which will give me an option to send it to any email I want. I type my Outlook email and it will send all my pictures as easily drag and droppable attachments in my Outlook.
It's dumb that a multi-billion dollar company can't just fix their stupid app but that's how you get around this frustrating issue.