Why not check out observation checklists? You may be able to use it and save a step of uploading documentation. You may also be able to get down a workflow of using assignments with courses for uploading documents like spreadsheets.

Is the assessment then happening outside of the LMS platform?  If so, it sounds like the External Training Activity app might be useful. 

You can configure additional fields on the External Training Activity so that you can list the specific equipment type.  And this app allows you to upload files to associate to the training record.  

Here is the help article associated to the app:

https://help.docebo.com/hc/en-us/articles/360020083460-Activating-and-Managing-the-External-Training-App

Between @Annarose.Peterson and myself - we can get you there.

Consider your workflow and you may be able to achieve 1:1 for what you have.

Only other thing I would say to think about:

Always ask yourself and your team are you actually improving anything (beyond digital record storage and direct reporting relationships) when yawl are looking to kick off a new object/approach in your next iteration of the “learning object” in the new LMS. ..good luck with this. Let us know how it works out.

If you have a need for a scoreable form where the instructor fills everything out on behalf of the student, I can describe the solution I built for that using Cognito Forms, some (unsupported) JavaScript, and automation.