I would llike to see ArcPad be able to synchronize photos with ArcGIS Server live from the field. This would work in conjunction with the ArcPad for ArcGIS Server extension that currently allows you to synchronize data edits from the field. Based on the help docs for ArcPad 10, syncing photos is still a process for manual check-ins and defining photo options is not supported when creating a project for ArcGIS Server.
