TL;DR - Free plan (previously called personal) now let’s you have up to 3 team members - 100 devices - Monthly paid plan also now includes 3 free users - Additional users are PAYG Very refreshing to see a company give more free stuff after adjusting their plans. Usually you see the opposite.
TailScale is still small. They probably identified that their pricing plan was preventing them from user acquisition and/or they are having pressure from competition and thus are trying to flood the market to become the de facto solution.
It’s a pretty common play for a smaller startup. They just broke the 1B valuation last year. Could be the board pushing the executive team to grow the number of users because happy free tier customers tend to convert to paygo at some non 0% just as paygo customers convert to ENT contracts at some non 0% as personal projects grow into businesses and smaller businesses grow into large ones.