If you plan to use Pages or Numbers for this project, you will have to purchase the cute graphics separately. There have been some discussions here on how to facilitate making the calendar pages, and maybe you can find them by searching the discussions. It seems to me that Numbers would offer the most opportunities for automating the placing of the days of the month in the grid, but that may be only because I'm more familiar with Numbers. The main consideration for me is that Pages can't have references that stretch from table to table.
Pages can do just about everything in your screen snap with a bit of work. eg the calendar will need to be done in a table and filling in the correct dates is only partly automatic.
The graphics however will need to be done in a drawing program, like the "november" and imported as a pdf.
If you are exporting to a final pdf for printing by a commercial printer, the shadowing will be a concern, Pages outputs those at a low 72dpi.
Swift Publisher 3.0 has a calendar maker built in and might be worth exploring, it is quite cheap and has better export to pdf.
Sounds like Pages isn't the way to go to make it super simple. I'll search the app store for third part stuff maybe and hopefully I'll find something there. She was using "My Memories Suite", but it was a pain and never saved any of the items that she wanted to save from year to year.
I guess it comes down to if anyone has any suggestions of an easy app that can create something similar. I'll check out swift publisher 3.0...thanks for the suggestion!