Help developing img cropping tool in python

[Mekire]

I would myself definitely use for loops rather than while loops for this.
Also you need to reexamine what arguments Image.crop takes.

You wrote:
new = img.crop(vert_to_counter, vert_to_counter, 72, 72)
Firstly it takes one argument that is a tuple, and secondly the last two parts of that tuple are not height and width but rather, right and bottom of the desired box.
crop = img.crop((x, y, x+width, y+height))

If you can give me a full rez copy of one of your images I'll try to give you an example implementation.