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Well I really do not know what the issue could be other than that you are using VS 2015 that has had many bizarre bugs reported.

The only suggestion I can offer at this point is load all values...

Well that is strange! How can it be True in one view and not the other?
Try adding this right after the "For i As ..." statement.

Dim typeName As String = "Nothing"
If...

Please do not PM me to respond to your posts. I will reply if I have time and feel I have something to offer.

Without knowing how to column is configured (TriState, TrueValue, FalseValue,...

All data types derive from type System.Object so an Object type can hold any value. This is why the DataGridviewCell.Value property is type Object. Instead of trying to find some object to...

Add:
Option Strict On
to the top of your code and fix the identified problems.