These guys, http://bermanvc.com/ are really smart. They invest in real estate related technologies and even invested in YC alum 42floors.
Usability is among the worst you will find. This is particularly egregious since RE is filled with some of the most technically incompetent people you've ever met. Some real estate agents are fantastic and have found their calling in that job, but the overwhelming majority of the ones I met ended up in that industry by accident. I tend to joke that if you're too incompetent for all other careers, go ahead and get a real estate license.
One of the biggest problems is that not one solution I've ever used considered flow. They solve small pain points, but none are workable into the more complex workflows that need to be accomplished.
If you really want to understand how an agent works, focus on their calendar. 90% of their work involves coordinating many activities for a listing. You can also try to get ahold of sample files for east listing that brokers will keep (they are legally required to keep them for 7 years in NC. I expect a similar requirement elsewhere).
In short, no you don't need to get a license, but you need to be a Sherlock and know what questions to ask to gather all the evidence you need.