Hi CLL,
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The RosterEntry attributes Operating Duration and Last Operated are set when a Throttle has been obtained BY ROSTER ENTRY ( not just DCC Address ) and this Throttle is released.
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Larger Rosters could well have 2 entries for the same DCC Address, it's not a unique field.
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If there was demand for it, it would be possible to add an option to update Roster Entries matching the DCC Addresses when a non-RosterEntry selected JMRI Throttle is released, although JMRI already has a fair number of Throttle settings and there's been no demand AFAIK.
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An option to update matching DCC Address RosterEntries based on locos within command station monitors would require a fair few code tweaks.
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Steve.