Writing to a file is very similar to writing to the transcript. You need to open a writestream on the file, then you write to it.
If I were writing the data out, I'd probably try to write it out as a CSV (comma separated values) so that I could read it into a spreadsheet.
If you want to make it easy for people who don't like computers, perhaps you should make a GUI for it. The GUI might list all the drawings in the top pane. When you select a drawing, you get to see its contents in the bottom pane.
I assume that when you run drawn2012 it returns some kind of data structure that gives you the drawing for 2012?
My son had something like this. He had his program send each person email, telling them who they drew. If you wanted to do this, you could focus on how to send email instead of on how to make a GUI.
I'm not sure what your motivation is here. Is your main aim to learn a little Smalltalk? To make a useful tool for yourself? To make a useful tool for someone else? These are all worthy goals. My advice would depend on your goal. And of course, goals change. You might have started out just wanting to learn Smalltalk but now you just want to make a tool that someone else can use so you don't have to be in charge any more.