Anyone know of a way to set the system to automatically pass documents from the request to the project after conversion?

Is there anyway to keep the planned completion date on tasks that have been completed the same if you update the Planned Completion Date?

I'm looking for a way to require documents be uploaded before a task can be marked complete. I know its not truly possible, but looking for some type of workaround to have a question be required to say they uploaded the document - I know you have to click into the custom form to verify though.