At Notion, we used to have a limited free plan where we only allowed users to create 1000 blocks (pages/paragraphs/embeds/checkboxes/database rows) before we directed them to upgrade to the "Personal Pro" plan. Supporting free users dealing with the block limit was a major headache, just as described in the OP, but more importantly the Personal Pro plan was kind of a dead end - few users converted to Pro, and those that did weren't worth much, since the Pro plan is pretty cheap and doesn't have much network effect.

We took a hard look at that free personal plan and how it worked with our goals. Instead of phasing it out, we decided to make it unlimited - now personal users can make as many blocks as they want [https://www.notion.so/personal]. But importantly, we also switched up our segmentation at the same time: we restricted the personal plans' collaboration model and created a new "Team Trial" plan, with the same 1000 block limit, but with all the teamwork features included. Another thing to note about our Team Trail is that it's not time-limited at all, teams can keep trialing Notion until it has clear value to them. We have many fewer users frustrated by the block limit, but those who are are much more valuable, and are getting a lot more out of Notion -- when they upgrade, it's to a Team plan with strong network effects and a path to future expansion.

And all those (now) very happy users on the free plan? They're like jonpurdy [https://news.ycombinator.com/item?id=26059666] - they'll take Notion into their (future) teams and workplaces, even though in the shorter term they're a strain on our systems.

My advice is - there's more nuance to this than "MAKE IT FREE" vs "DON'T MAKE IT FREE". Think about how you structure upgrade incentives around value, and about how your free plans fit into your overall market strategy.