Hi Ivan,
to have two upload, you need to place two dataview and place upload image widget in each , as upload image widget takes system image of dataview inside which it is placed.
To show two image i would suggest you to go for image carousel widget
Good luck!
If you want 2 separate dynamic images on a page, I would suggest you create another entity, named "ImageHolder" that generalizes Image. Then create a 1->* association from your parent entity to this one. You can then create as many "ImageHolder"s as needed, each one with the ability to upload and show an image.