It seemes that WPF being made for database binding anyway, so all nulls had to be a DBNulls. So, you still have an option to add blank values in you ItemsControls: just use DBNull.Value.
Should look something like this:
static public IEnumerable<Contractor> Contractors
{
get { return ConditionalGetObjectSet<Contractor>(); }
}
static public IEnumerable<object> ContractorsWithNull
{
get
{
List<object> result = ConditionalGetObjectSet<Contractor>().Cast<object>().ToList();
result.Insert(0, DBNull.Value);
return result;
}
}