Python program that makes cutlines for images - program half made - need finish -- 2

I am looking for a Python programmer to help me finish a program I have started. The program's main purpose is to create custom cutlines for images. The ideal candidate should have experience in image editing and batch processing. The program should be able to support JPEG and PNG file formats as well as pdf. Additionally, the user interface must be graphical, so the ideal candidate should have experience in creating GUIs. The program is halfway complete, and we need someone to finish it. There is a gui already, and the functions to create a basic outline from an image.

What we need:
1. the functionality in the program to take an uploaded image, create a single cutline postioned a user defined space apart from the actual image ( 0.16 inches) or no space on border at all.
2. the functionality in the program to make that cutline multiple lines instead of just one encompassing the whole image to create cutlines on the inside of the image, for negative space in images.
3. The ability to see the created cutlines on the uploaded image in the gui before the image is created and saved and the ability for the user to save it as a jpg, png, or a pdf.
4. The ability to also upload a pdf, jpg, png, AI, PSD, or EPS file as the starting image.
5. functionality inside the program to dictate the shape to be a square, circle, or rectangle with the uploaded image th exact center of the basic shapes.

These all should be user controlled options inside the gui. The program right now has a gui, uploads an image, and you are able to create a negative space cutline. This is only a portion of the end program. We need your help to finish these function inside of this program.