Application to Arrange Words into Alpha Numeric Characters Fixing Bugs Adding new function

We are a printing and embroidery company in the UK. We sell a type of product called a leavers hoodie where we arrange all the names of a group of people into the shape of a number and then screen print them onto the back of a garment. I have an example back print here: [url removed, login to view] I have a video of how we currently do this using adobe illustrator here: [url removed, login to view] I have also attached a word document outlining the procedure. We're not precious about the language the program is written in, but it must be a standalone application, either web or windows based. Platforms or frameworks such as Java or .NET would be acceptable. We would want to feed all the names into a text box of some sort, and then choose between an 18 with no border and an 18 with a border. I have attached pdf's of both template designs to the project. We would need the whole source code given to us on completion of the project.