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It sounds as if you need to set up some sort of script, that would go forward through Outlook's Calendar and mark some days Off according to the pattern you have mentioned. Perhaps in VB Script.
But looking it up, it seems that to build the calendar as a pattern in MS Excel, then import it into Outlook's Calendar, might be simpler and work. See this page:
viewing the work days as repeated appointments, and building the pattern something like this:
as the formula, where cell A2 contains the starting day of the calendar, then '6' for 6 work days, then F2:F147 as a range of cells containing the 'holiday days' that would be the Fridays or Mondays off, on that schedule, and also the '2 days off after every 6 work days' that the schedule would need.
Does that sound workable to you, and which way would you like to proceed?