I did a quick test yesterday with 1 image and it uploaded to the custom folder I specified. That didn't seem to be the issue. The issue was not being able to edit or remove them like shown in the screenshot I posted.

This happens with or without setFolderName(); being called.

I think I got this working now. Using the many_many relationship instead of has_many as I got the path error bug as well.

Then I removed the $this->Images() from the UploadField and everything is working and I can now edit/remove images attached to pages.

I did find another bug I think in that setFolderName() can't take spaces. When I use 'FolderName' it doesn't create a folder with a space in it like I thought might, so I tried doing 'Folder Name' and while it creates the proper name with the directory being 'Folder-Name' uploads fail for some reason. URL looks correct but always 404.

finally

Thanks @thi3r
Thanks @Hattori
Thanks @Liam for the final solution

One last thing.

How do I access the variable in a loop?

I have this

<% loop Images %>
   <a href="$SetWidth(800).URL">$CroppedImage(160,160)</a>
         
$Image.Width
<% end_loop %>

$Image.Width is what doesn't work, everything else is fine. Tried a bunch of var names and nothing works.