Harbormasters in Maine are picked by each town. Usually in an informal polling of the folks that use the harbor with a finger on the scale for traditional local uses. IE, if its been a fishing harbor or fishing / sailing harbor then those will be prioritized over large motor driven summer yachts.
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Some are elected by the town. People usually serve for many years as no one wants to lose institutional memory and have to retrain staff. Some are paid well on taxpayer cash, some are almost a volunteer position (mostly on islands where cash is tighter). Almost all are well loved or they don't last.
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Platners rep is good from the guys n gals I know who fish or dive downeast in Hancock County. He clearly inspires basic confidence in the rougher coastal types as he looks like the kinda guy who can stand his ground and will do what the community needs as circumstance demands. IE a fighter.
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