FREE → $9 → $19 is probably not the pricing strategy you think it is. This is one of the biggest leaks I see when I audit free → paid communities. We get nervous about asking people to pay, so we start really low. But if I’m already getting value for FREE, why would $9 suddenly make me want to upgrade? There needs to be a meaningful difference between Free and Premium. I’d rather see you start Premium around $49/month and increase it by $10 as the community grows, eventually capping around $99. You don’t need everyone to upgrade. You need the right people to see Premium and think: Yep. That’s where I need to be. Price for the transformation, not because you’re afraid people won’t buy.