How would you assign groups and/or individuals to an item?

I apologise in advance if this is rather vague, I'll give as much detail as I can.

In our software, one of the tasks the user needs to perform is assigning people to an item in order for those specific people to be able to purchase it. They can either assign groups of people (pre-made groups), or individual people.

Once they have assigned people to the item they can then give individual people discounts by applying bursaries and allowances.

Assign people step in wizard

As you can see this is the final stage in a wizard which allows the user to create the item these people can pay for.

(A little side note, the 2 input fields in the top section will be typeaheads - see below , allowing the user to search for groups and/or individuals)

Typeahead design

One of the problems I am having is that this is a redesign of a current system, adding in new functionality. As part of the previous version when the users assigned people to an item they would use check boxes to indicate who is assigned and who is not. I have changed the use of the checkboxes, so now everyone in the list at the bottom is assigned, they need to physically remove people using the remove button. The checkboxes in my design are used to bulk apply allowances and bursaries or to bulk remove people. I have tried adding instructions, however it is well known that "users don't read" (a ltitle mantra I follow)!

So my 2 questions:

  1. Does anyone have a better way of assigning people to the item?
  2. Is there a good way to tell the user that the checkbox is no longer used to indicate who is assigned and who is not?