Nick
I'm not sure why you need to change the WF field to a text field? You can have a dropdown be multiselect in Workfront, or you could use a checkbox field as well.
The easiest way is to leverage the misc. action module for your issue, and select "assign" or "assign multiple", whichever you are trying to do, then map in your assignment and your user you want to assign.
The originating scenario will actually wait to proceed until it recieves a response from the secondary one, so if you need some data out of that one you can set up the secondary to respond with that data.
A document can only exist on a single task at any one time as far as I'm aware, but you could for sure leverage fusion to move documents from one task to the next as required.
To make sure I understand, you are trying to update one of a parameter's options? If so, how are you making your call? You shouldn't need to do any of this when making an update, because your update shouldn't be in the url.