I need a way to generate individual PDF reports for all the data collected for each manhole in a database. I would end up with hundreds of reports, one for each manhole in the feature class. The report needs to selected attribute data such as manhole type in a chart along with 1-3 pictures and possibly a small map. It doesn't look like the reporting tool built into ArcMap can make something this complicated. Any help would be greatly appreciated!
Assuming you already know (or are willing to learn) Python, I would recommend looking into the open-source Python ReportLab Toolkit libraries. I have seen a number of Esri presentations that have incorporated it into their processes for on-the-fly, custom report generation.
There is also a spinoff library called Geraldo, which "is a reports engine for Python or Django applications. It uses the power of ReportLab to generate reports with page header and footer, child bands, report begin and summary bands, agreggation and graphic elements, etc."
You should be able to incorporate these libraries with DataDrivenPages and arcpy.mapping.