In my case if two users add an item at the same time they will both have the same orderID and will be ordered by name. After I have binded the objects to the list I then go through and set there orderID in the DB. Once the page finishes the post back from the add button they will have increasing orderID's from the top down.
I'm not sure how your going to use the Pkey, if it's not identity then you have to insert the key manually every time. Your then back to the same problem, your not going to be able to tell if two people are adding at the same time, if they do and they both are trying to enter the same key one of them is going to get an error.
I'm also kind of confused as to why you have two users doing stuff to the same list. That doesn't make much sense, one user would reorder the way he/she likes and then on the next post back the new order will show up on the other user and then that user would change it to their liking and so on. Or user 1 would add an item and user 2 would see that item and not like it and remove it and so on.
Tim