If I understand the problem correctly I would restate it as:
There are dashboard items (DashboardItem) that can be displayed on a 
dashboard.  There is a relationship between user groups (Group) and a 
subset of dashboard items defining which dashboard items can be displayed 
for that group.  You want to add a relationship between the user (User) and 
the subset of dashboard items that are available to the group and allow 
them to choose which of those items will be displayed on their personal 
dashboard.

If that problem statement is correct then you would want to do something 
with a HABTM relationship between DashboardItem and Group as well as a 
HABTM relationship between DashboardItem and User with the limitation that 
only items that satisfy the constraint of being in the list of 
DashboardItems associated with a particular group are available to be 
included in the DashboardItems that can be associated with a User.

You will probably need custom code in the afterDelete and afterSave 
callbacks of the group_dashboard_items model that will update the 
user_dashboard_items model to remove or insert additional relationships.

This does not address the actual content of your DashboardItems which would 
presumably be generated on the fly from other models (as others have 
already pointed out in their responses).

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