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All of the stories Michelle is telling Conrad occurred during season 1. However, Nancy Stafford (Michelle) did not join the series until season 2.
In the original airing of 'The Judge', Matlock's client's name was Kevin Meredith. When Michelle tells the story to Conrad, his name is Jim Meredith. In the original airing of 'The Sisters', the uncle's first name is Harold, but when Michelle talks to Conrad, she calls him Howard.
Manteo has a town police force, so any crimes would be investigated and charged by those officers. The sheriff's department would not normally be involved in criminal matters that occur within the city limits of Manteo but would instead focus on matters in Dare County instead.