You cannot use configurator to distribute data to individual devices, only to set which apps you want. The apps do not 'contain' the data, the data is stored separately on the devices.
I cannot, right now off the top of my head, figure out how to copy data from an app onto lots of devices.
If I understand you correctly, you want to install apps on iPads without having to wipe them when you Supervise them is that right?
Unfortunately, when you Supervise a device it will always wipe the iPad. Your option with Apple Configurator is to leave the device Unsupervised and install configuration profiles and apps that way.
Another option would be to use an MDM to wirelessly install configuration profiles and apps. Note that for wireless app distribution the end user will need to enter in their own Apple ID and their Apple ID will "own" the app. One free MDM out there is Meraki Systems Manager. Try it out… it'll be a good introduction to wireless mobile device management and its free.
The file structure on iPads is different from Mac OS or Windows. iOS apps sandbox their data so distribution of data can be tricky and may not be possible in all cases. However, whenever I share data with others I use Dropbox . Many iOS apps have Dropbox integration and its a great way to share information between devices.
Hope this helps!