Hay,
I spoke with Tech support about this issue. The attachments not being available on the iPad has to do with our network setup. Forgive me, I'm not a network guy, so i don't fully understand it.
Our GIS server is in a NAT subnet which is some how creating a loop. The way I understand it, the loop isn't created until the iPad is disconnected from the GIS Server. When the iPad is reconnected to the GIS server and the attachment is requested, the loop exists, not letting the attachment out and onto the iPad.
ESRI also said I should use ArcGIS Server to implement security vs. however we were doing it via the network.
Sorry I don't have any more specifics. Working with our network guy, hoping he figures it out.