One of the best indicators of writing and drawing development (in my experience as a kindergarten teacher) is a child's ability to write their name and draw a picture of themselves. A child's name is usually the first word they learn to read and write.
In our classroom we ask each child to draw a picture of themselves and write their first (and later on in the year) their last name(s) on the first school day of each month. This way we can show the progression of their writing and drawing development over time and use the information as observation for assessment purposes.
This file contains printables for teachers to use each month of school, with a separate page for notes to be taken on the child's work (e.g., hand preference, pencil grasp ability, time spent on task, eagerness to complete activity). These pages can be stapled together into a booklet for children to complete, or can be used separately as dividers in notebooks or portfolios.
Not only are these printables a great source of information regarding children's drawing and printing progression over the year, they double as a keepsake that families will treasure!