stockton 10 Light Poster

My organisation is about to deploy 500+ Raspberry Pi's(running Debian) across the country. I have been given the task of configuring these devices. Configuration depends on specific installation, so cannot be configured before installation and the staff at the remote site seriously lack skills. BTW These remote sites are all over Southern Africa.
Each of these remote sites will be connecting these Raspberry Pis(RPi) to a Windows server which will be on an Intranet(No internet access).
I think that I need a program, probably running on the aforementioned server, to make the configuration of the RPis as fool proof as possible so that the remote staff may do the configuration that cannot be automated.
My background is Linux(so the RPi's are not an issue), languages include C, C++, HTML and PHP. Not much Windows.
My initial thought on program development is HTML but connecting to each RPi without knowing its IP would be a challenge. On Linux I could do something with ntop but how to do this on Windows?
All suggestions on how I should proceed are welcome.

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