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Dealer will only do it if asked, or if there is a problem that the software corrects. For example, if you go to the dealer for a suspension problem, and they replace a part, they may not look to see if your PCM/BCM is up to date with the latest calibration.
By law, a manufacturer cannot say that every H2 that comes through the door of a dealership has to be reprogrammed; the minute a manufacturer says that, it is considered a campaign. However, a manufacturer can issue a bulletin that states if the vehicle exhibits this problem....reprogram to the latest PCM calibration.
In regard to the calibration, they are cumlative. Example, version 1.1 fixed one problem, 1.2 fixed another, then you have 1.3 added, the latest version 1.3 will also include the fixes from 1.1 and 1.2.