There are a number of variables involved so I'm afraid it really isn't clear
exactly what you're trying to accomplish, what you're expecting or how
you're going about it, but here are a few comments. You can refine what it
is you want to do from there:-)

Yes, it's true that if you Insert more than 1 image at a time with some form
of Text Wrapping set as the default the images will be positioned directly
on top of each other. I know of no way short of a macro to change that.

However, if you set the default (Word Options> Advanced> Cut, Copy and
Paste - Insert/Paste Pictures As:) to In Line with Text, then use Insert
Tab> Picture, Contol-Click each of the files in the *reverse* of the order
in which you want them inserted, then click OK...

Each image will be inserted into a separate, successive paragraph. How many
"pages" that generates depends on how big the pictures are. However, as you
resize the pictures the doc will repaginate accordingly. You can then change
the Text Wrapping for each image to whatever it needs to be.