I need to have optional documents that a driver can choose at a stop

I have documents setup for Route. In this example they arrive at a stop.
1.If it is a pickup, I need Loaded Info, Arrival, Depart, BOL, Pieces and Weight etc.
2. If it is a delivery, Empty Info Arrive, Depart, Who Signed For It, etc.
3. If They Are Delayed For any reason, send us a notification, a time delay started, notes, etc.
4. If there is an issue with the stop, wrong address, damaged freight, facility closed etc. I need info to
process in our dispatch system

Under workflow I created Tasks for each stop. There is two problems with this
1. The task don't display the document name, just document 1, document 2, document 3
2. They have to complete task 1 (document 1) before they can select document 2, etc.