Option to add observation checklist to uploaded assessment.

Hi Team, 
We have students submitting post course work / evidence and we would like the option for the trainer to review that document and complete an observation checklist in the one assessment. 

Ie. Currently, students can upload a document - but I can only choose S or NYS - I am unable to have multiple items for that one document. ie. SLAM uploaded, hazards identified relevant to task and location, control measure applicable, SLAM signed by supervisor etc.. 

To counter this we have either created an observation checklist as another assessment in the system or as a word document that is uploaded as evidence with the feedback.