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Maybe do not try to figure out, what visitors to INclude, rather search visitors to EXclude. but you need to create 12 segments based on 12 custom date ranges...

preparation: date ranges and segments for month in the past

  1. create a custom date range (if not already available) for every month in the past
  2. create a corresponding "hit" segment with just the date range in it

final segment

the segment would look like this:

visitors (exclude) where

  - visitor container: (segment "last month") visits less than 5 or

  - visitor container: (segment "2 month ago") visits less than 5 or

  - ...

what it does: you search for any visitors who had not 5 visits in one of the last 12 months. and finally exclude all the found visitors...

attention: be aware that using date ranges affect the results! even if the final visitors had hits outside the last 12 month, they will not be shown. the reason is somewhere in the backend that the segment only returns hits for the dateranges you use in the segment ... sounds strange, but it "works as designed"