You're absolutely correct, and the answer to the second 'why' is that the sales process in education is unbelievably long and expensive relative to what the cus

You're absolutely correct, and the answer to the second 'why' is that the sales process in education is unbelievably long and expensive relative to what the customers are willing to pay for software. I worked for an education startup between 2003 and 2006 that made a learning management system similar to the OP. We also laughed at the terrible UI and outdated technology used by our competitors. Little did we know... The problem is that you only have two choices in education. You can try marketing to individual teachers using Adwords or the like, but there aren't many teachers who want to spend their own money on classroom tools. Districts aren't keen on it, either. This is strictly microISV territory. The other alternative is to market directly to school districts or universities. That means you need expensive sales reps and money to burn on travel budgets, trade shows, etc. The sales cycle takes about a year, even for the smallest customer. Your customers are the administrators on the purchasing committee, not teachers or students. The admins are far more concerned with back-office functionality like tracking attendance or whether teachers are following the curriculum than the quality of the UI. In fact, the UI was basically irrelevant so long as it was physically possible to do everything on their list of requirements. Educators make it extremely expensive to provide them with software. But they don't have deep pockets either, so the margins for software developers are extremely tight. There are no competitive pressures in education. Districts are perfectly happy to use obsolete technology indefinitely. There are still thousands of schools using applications based on Access, Foxpro, and DBase IV. (seriously!) The only thing in your favor is that once you sign a customer, they are extremely reluctant to move to a competitor regardless of how outdated your product becomes. Thus, the standard business model in education is for the large players like Pearson or Blackboard to gobble up small independent companies with locked-in customer bases built up over many years, cut investment in new development to a minimum, and milk the products until they're unviable. TL;DR: The people buying educational software don't care and won't pay for good UI.