Auto-Updating Dates in a Diary/Calendar

I've a script that will do the planner pages (e.g. page 1 and 2) of your PDF, but so far as the daily pages go, the information such as 1 January Wednesday can all be one threaded textframe, with Excel doing the heavy lifting of generating the dates. However, the three calendar panels will be harder to do, these I'd treat as images that are in a parent page relevant to the month at hand.

Another method might be to look at using data merge to make the pages, where - again - the data for the dates comes in from Excel.

For the last 10 years or so I've been looking to automate diaries in a completely foolproof way over a collection of 250 SKUs. Unfortunately there are so many variables in play that a one-size-fits-all solution. To be clear, that isn't just the dates such as 1 January Wednesday, but also the school terms associated with the weeks; the mini calendars, the front matter... it's a massive task.

I handled the elements that follow each other (such as numbers in a calendar) using separate text frames that are linked across the pages of the document. This way, if I add or remove characters in a frame, the sequence automatically adjusts. So far, I haven’t found a better solution.