This idea has been developed and deployed to Canvas
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https://community.canvaslms.com/ideas/8778-docviewer-updates
Tool secection is granted on a one-time basis. When you select the Free Draw tool and start drawing, the Free Draw tool remains selected during the drawing of that one line, and then the tool selector reverts to the Selection tool. For an instructor to make a multi-line Free Draw object, or in making repeated use of the Highlight or Strikethrough tools, they will have to re-select the chosen tool after each use.
Please consider making tool selection "sticky" to allow for multiple use.