Speaking as a teacher, while your 5-points are very good, there's a happy medium here you can hit between free and paid.<p>Individual teachers have minuscule discretionary budgets (either $0 flat or up to a few hundred for everything). Departments in a school have a bit more (usually hundreds to thousands once textbooks are paid for). Schools and school districts have more money to talk about.<p>The pace of adoption is the exact opposite. Teachers are willing to try something new, and will show it to their friends/coworkers if it's awesome. School districts are slow to adopt new technology, and rarely turnkey it to other district (schools have their own NIH syndrome).<p>You want to find a way to make the individual teachers happy and seek out your tool, but also give them a reason for their supervisors to want to pay you. Think about what an org chart for a school would look like. Each teacher has 15-150 students who report to them. They'll collaborate with the other teachers, and all report to a supervisor, who has their own boss(es).<p>In a school, you'll probably either want to hit the collaboration between teachers or easy metrics on student performance for the big bosses as your pain points. It won't stop us from using your program for free, but it'll give the people with money a reason to want to implement it in the entire school.