With PRTG Scheduler, you can configure customized maintenance windows for every PRTG object (Sensors, Devices, and Groups). It allows for various ways of occurrences, like every first Sunday in January, February and March, or only the first week of every month.
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Can I run the application on a dedicated webserver? #6
Not as of right now, as it needs to modify the js_custom.js file to inject the menu entry and write the report file to PRTGs webroot folder.