Thank you so much for your help!
We've found that creating layer files of all of our TIF allows them to be brought into the map when the hyperlink setting is set to document with a field that holds the path of the layer. In a new map, it seems that this method works fine. However, in an existing map with mutiple layers already, the only way I've found it will work where:
A. There are no overlapping Polygons (this is no good for us, we have several different images sometimes for the same area)
B. If, when the layer chooser window comes up after clicking on overlapping polygons, If I click Jump, and then Close very quickly, the image gets added to the map, but not if I just click Jump. I thought this was sort of odd.
I've been trying to work through what someone else posted in reply to the same question I posted in the Python forum, but I'm having some trouble getting the last part of the function to run. As well as figure out a way, like you said, to emulate the functionality for the hyperlink script in vb.net, but I didn't realize I couldn't do any geoprocessing calls in that.
I hope you can find some time to port that to an add-in, I would super appreciate it, I'd owe you a drink at the UC.
Either way, thank you for replying, this is a problem we've been working on for a long time now.
Ross Wiseman
GIS Technician
City of Fayetteville, AR