Requirement: Boss wants an email on the 14th of the month and day before last weekday of the month with a status update. This is so the boss can combine and submit the information on the 15th and last weekday of the month.
Reoccurring Outlook calendar entries can apparently take only one pattern. There is no way to make one calendar entry for multiple patterns. I cannot make one for say both the 14th and 28th or even worst the 14th and last weekday.
There is no concept of day before last weekday or day. At first, I looked at setting the reminder for the 28th, which could be the day before the last day of February in a leap year and last day of a non-leap year. However, it would be as many as 2 days too early for most other months.
Reluctant Solution: Set the entry for the last weekday and the reminder for 2 days prior. I get the reminder in time even if the date is not ideal.