How can I upload multiple photos without using an app?

I'm a special education teacher, and I teach a photography lab that teaches students how to scan and edit photos. We use the school's set of Ipad2's in order to crop the photos since the majority of students I have don't have the hand eye coordination neccisary to crop using a desktop computer and mouse. The problem I'm running into, however, is that our IT department wont let me download any apps onto the iPads. I've asked on six seperate occasions in order for them to update the iPads to ios7 and to give teachers the permission to install apps-- the first request coming at the start of the school year-- and they havent responded to any of them, so I'm not holding my breath.
Currently, I'm uploading all of the photos my students scan to my personal dropbox account, and the students access that and download each photo individually onto their ipads. Not the easiest thing for special education students to do, but its doable. I have not found an easy way to get the cropped photos off the ipads, however. Any ideas? I could attach each photo to an email, allthough thats more trouble than its worth most times. Dropbox will only allow me to upload one photo at a time, and keeps overwriting the photo I previously uploaded with the new one if I try to upload a second photo. Photo stream is the obvious answer, but icloud is disabled on all the ipads and only IT can turn it back on, something they've been unwiling to do

I worked in IT on the university level for four years so it's really frustrating to see more safeguards in place in a public school district any university. If we're trying to teach these kids to be ready for real life and then block out and don't let them use half the technology they're going to encounter in real life, well I just don't get that. But that's another rant for another time.
How I do it is I save all of the photos my students scan onto my external hard drive, then transfer them to my personal computer and upload them to dropbox using Dropbox for windows (or whatever the desktop application is called) . I then have my students go to dropbox.com on the iPad, login as me, and go through each photo, saving each to the iPad as they go.
I should have said upfront that when I try to connect the iPad to my personal computer it charges the iPad but won't recognize under my computer or show up in iTunes, so I am unable to see any of the data on it. I'm pretty sure it's not the 30 pin connector that's malfunctioning because I've tried with two of them. I can only check if it registers with iTunes on my personal computer because I can't download iTunes on school computers since I don't have administrator privileges

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