I should add that all the images are in the 200 to 300kb range as well. They aren’t massive files.
I have this same issue with my own posts and inserting images. It’s been super annoying. If I go into Inspect/Console I see this error if I try to put more than 7 at once:
jquery.js?ver=1.12.4-wp:4 POST https://blog.MYWEBSITE.com/wp-admin/admin-ajax.php 500
Any idea as to what it means/what to change to fix?