In Word, you can perform logical comparisons in a table using formulas. A formula in Word updates automatically when you open the document that contains the formula.

The problem is that whenever I insert a new picture somewhere and add the caption, the figure numbers below the one I just added don't automatically increment. I have to manually update them.

Fields that don't update automatically pose a problem with many users because they don't remember to update them manually. When you need this functionality, use this VBA procedure.