I've been testing both free and paid project management software for my small agency over the last two years, and the free tiers are surprisingly capable now. We run three client projects simultaneously with a free plan and only hit limitations on file storage and advanced reporting. The real question is whether paying $20 per user per month adds enough value for task automation and integrations, or if that money is better spent elsewhere. I lean towards saying most teams can stick with free tools until they hit around 15 employees, but I'm curious how others justify the upgrade cost.