Adding interactive map to PDF?

I'd look into geoPDF it allows embedding a georeferenced data in a PDF and can handle everything you've asked for.

I'm not sure on the ins and outs of creating one, but might be somewhere to start from.

Linky : http://www.terragotech.com/products/terrago-toolbar

I'd certainly go for PDF, and use FME to create it - with FME you can turn any spatial data into a 2d or 3d PDF.

Click here to see how FME works with ArcGIS

The display images I'm not so sure. You can create links on a PDF, but if they aren't connected to a network that doesn't help.

However, I bet you could write the images separately into an index in the doc, then write references to them.

(Disclosure: I am an employee of Safe Software who make FME.)

ArcMap (I'm using 9.3.1) is able to export a multi-layered PDF from an MXD document. In the File menu, select Export Map. In the dialog, select PDF as type, and, at the bottom, switch to Advanced tab. Set Layers and Attributes drop-down to either "Export PDF Layers Only" or "Export PDF Layers and Feature Attributes" depending on your need. Check Export Map Georeference Information if needed, then hit Save. In Acrobat Reader (I'm using 9), the Layers navigation panel on the left should be accessible. Enable it and the you'll be able to turn layers on and off.