I Haven't Seen One Single Update For Mac
No, that is not possible due to OS limitations. Just as not being able to open multiple documents at the same time from the File Open dialog. There may be a means of doing so with a VBA solution but I haven't seen one provided for Word 2016. Correction: I did overlook the fact that the dragging capability was added by the 15.36 update. Multiple images now can be selected in a Finder window & dragged into the document all at once. Additionally, you now can select multiple thumbnails in the Photo Browser ( Insert Pictures Photo Browser) & drag them into the document as well.
I Haven't Seen One Single Update For Mac Pro
What still does not allow inserting multiple images at once, however, is Insert Pictures Picture From File. For some reason it continues to permit inserting only 1 at a time. I had based my initial reply on only this method. Please mark HELPFUL or ANSWERED as appropriate to keep list as clean as possible ☺ Regards, Bob J.