I am being ask to enter National Guard Annual Training and Drill pay. How is this different that the amount already entered from my W2? Do I enter it again?

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Yes, for TurboTax to determine if your military W-2 qualifies for special military treatment, you need to add your military W-2 when requested by TurboTax; then you can delete any duplicate military W-2 entered before requested and identified for special treatment. 

To delete a W-2

1. Sign In or Open TurboTax.

2. Select "Take me to my return"

3. Select "Search" or "Help" icon.

4. Type "W-2" and double-click on "Jump to W-2" 

5. Select "Delete" next to the W-2 you desire to remove.