I feel like Evernote is a prime example of the pains of trying to convert free users to paying users for the same features, something we see in many VC funded software from its era. Once you give something away, it's damn near impossible to take it back, even if you plead your case as honestly as Evernote did.
Evernote was great. Honestly, it was worth paying for. But they gave away the farm too early, and folks feeling like what they had was being taken away from them spurned a lack of trust. Obsidian made the smartest play by giving you the editor, keeping the files outside of a database so that they're portable (so they feel safe if they ever have to move away), and telling you that if you want to own the sync story that you can, but you can pay to have the cohesive experience on every device.
Evernote was great. Honestly, it was worth paying for. But they gave away the farm too early, and folks feeling like what they had was being taken away from them spurned a lack of trust. Obsidian made the smartest play by giving you the editor, keeping the files outside of a database so that they're portable (so they feel safe if they ever have to move away), and telling you that if you want to own the sync story that you can, but you can pay to have the cohesive experience on every device.