As long as you don't get too fancy. (can't wrap text around an illustration, for example), you can probably do this. Save as PDF in scripts, has an option to append the PDF to an existing PDF file. Thus, you might be able to set up several layouts and use Save As PDF in a script that combines the PDF's. Getting the pages to number sequentially without gaps is also possible, but can be tricky to do when you save as PDF from multiple layouts. The most obvious limitation to this approach is that each appended PDF starts on a new page so you have to factor that in when you set this up.
You are asking about Database Publishing.
In the past it was done with Pagemaker or QuarkXpress, today Indesign is commonly used.
Indesign is probably more that the budget allows.
The Google for "database publishing filemaker indesign"
You would expect some interaction between Filemaker Pro or Bento and Pages, but I have not seen any references.
With Automator, you can probably do the database publishing, but I have not found references to any easy solutions.
This site is worth looking at http://automator.us/examples-04.html
I helped a lighting fixture retailer set up a FMP and Pagemaker Catalog system, it was a difficult task but was amazing in operation.
EDIT - there is a link to Pages on the above page
The automated publishing example shown on this page can also be done using the Pages application from Apple's iWork suite. Download the Pages Action Pack and the Pages Automation Example Installer.
The Computer Guy, Seattle
For all but the most elaborate pages layouts FM is more that up to the challenge and it can be done all in FM. A lot will depend on how many listings you per page, will the number be variable, etc. I would just put the photos in FM as well and print to the pdf directly. FM's ability to massage data is very good for a db program, but plan on testing a bit. Until you have your final data layout plan you won't really know what is the best way to "massage it" Sometimes merge fields, sometimes a calc field. You can put text in a large text field and do the formatting in browse mode and it will print as formatted. As PhilModJunk suggests the append to existing will assist greatly and you can get 11 pages in one section. For page numbers just make a field and enter the page number you want and forget the auto feature.
One method that works for numbering pages in subsequent report sections is Table::gOffset + get ( PageNumber) this can sometimes be the only automated way if the preceding section of your report uses sliding fields as then the number of pages to the report are then not a function of the number of records.
This script can determine the value to use for gOffset by counting the pages needed for the preceding section:
#any find and sort required should be done first, then:
Enter Preview Mode 
Go to Record/Request/Page [last]
Set field [Table::gOffest ; Get ( PageNumber )]