Downloaded Annotations on a Student Submission PDF file

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Two Things

I'm having students submit pdf copies of my drawing assignments, (no problem).  I am able to download if necessary to view, etc. (no problem).  Since going virtual last semester, I have been able to use the markup tools on the screen to; highlight, circle & underline, add text comments, etc, which helps me out, although a little more difficult than handwriting it on printed form.  

So I was asked by a student if they could get a printout of the annotated markup, (download annotated button there in speedgrader), this seemed to work until I tried to open file to print (no markups there).  I tried several ways to view it, from download menu, folder menu, open with Adobe reader, etc.  The view would show the markup, BUT not on the printed form?  Is this a Canvas issue or something else?

Second - I also noticed that in submissions (from my students, and as a student) of the pdf files, only the very last submission "View Feedback" is available to students.  If the student submitted more than one and then came back and clicked "ReSubmit Assignment", afterwards he cannot go back and see the mentioned "View Feedback" of any previous assignment submissions.  If this is how I'm grading files virtually, how can the student see his graded comments on the annotated sheet?  I know there is a column in speed grader to added comments, but this doesn't pinpoint the mistakes I want to show them on the pdf file itself.  

I believe both of these things tie together and add to confusion for the student and complications for the instructor.  What can be done?