I use the CellContentClick event, which makes sure the user clicked the checkbox. It DOES fire multiple times even if the user stays in the same cell. The one issue is that the Value does not get updated, and always returns “false” for unchecked. The trick is to use the .EditedFormattedValue property of the cell instead of the Value property. The EditedFormattedValue will track with the check mark and is what one wishes the Value had in it when the CellContentClick is fired.
No need for a timer, no need for any fancy stuff, just use CellContentClick event and inspect the EditedFormattedValue to tell what state the checkbox is going into / just went into. If EditedFormattedValue = true, the checkbox is getting checked.