How should I use this library for user updates?

Occasional Contributor

Hello everyone,


I have an existing library with a Word document that requires manual updates by 5 users periodically. I have enabled checked-in and checked-out features for this document library. I want to be able to track/view who checked-out and check-in the documents. For the users, this Word document may or may not have attachments needed (a work order). I want to create a required metadata field [Work Order Needed?] (either inside the Word Document or within the library) to track Yes or No and if "Yes" possibly make the attachment field required. Please help. If you have any recommendations that I have not thought of, I will listen. 

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