Not sure whats doing here, but the binding works for the label in the data template but not the tool tip. Any help will be appreciated.
If this DataTemplate is the ItemTemplate for a ListView like you state, then you shouldn't need to set the DataContext on the ToolTip nor have a RelativeSource BindingExpression in your Label.Content binding. The DataContext should already be set by the ListView. That's why we use the DataTemplate.
Try just a regular binding for each: