Taskpaper is a great productivity application except for a couple of shortfalls. One of these is the lack of support for repeating tasks. The developer is open about this limitation. I’m currently handling this with Textexpander snippets. I have a snippet for each week of the month. Each snippet is a list of items that should be done around that time of the month. I have a section in Taskpaper which is called “Repeats.” Tasks which must be done on a particular day are currently in the calender. I don’t have very many of those. This works pretty well when I remember to trigger these snippets. This approach does not account for repeating tasks that occur every so many months or on other time intervals. There are applescripts which can work with Taskpaper and are found on the application’s wiki. These are a bit more complex than I want to deal with right now. My approach is simple and I currently like it.