[dhpye]

There are positives to the data-entry pain: once somebody's entered their data, they have a real investment in your system. Question banks can be reused and grown, so the pain does decrease over time. Depending on how easy or difficult you make it to export their data, it may help user retention.

For users zero to ten, you might want to consider taking this problem off their hands: let them upload a photo of a worksheet, and let the system "magically" transform this into the proper format. (ie, OCR the data, then edit it yourself or pass it on to mechanical turk). If they're not completely convinced of your value, even with this level of assistance, then you've got no market. If they do buy in, then you can figure out how much pain you can leak back into the system before they balk.

One potential value-add: math problems from teachers often have hard-coded values. Current test-bank software lets teachers convert these to formulaic question generators, but this is even more time-intensive of a process than straight data-entry. Applying some "magic" to this process is a ripe opportunity.