This is a really intelligent move on tailscales part. Yes, there are a few hobbyists who paid for the personal pro plan, I'm sure. But at $50 a year it's not exactly going to change the companies economics a lot. Then the next step was jumping into "Team" level which would actually be a major step down for a small hobbyist who wanted a lot of devices (Personal was 20 devices, Personal Pro was 100 devices, Team was 5x the use count. So 2 users... 10 devices). Realistically hobbyists are not going to be the bread-and-butter of Tailscale's business, so why not let them go crazy.
Looking at https://tailscale.com/pricing/ one of the other major changes that has been made, is the free plan now provides access to almost every feature. Going up to the $6/mo/use "Starter" plan actually loses you some features. So if you've had a taste of the good life, and want to keep it, but have more than three users… You are going to need to go to the premium or enterprise plans. Probably makes their sales process, super easy, since they don't need to give out trials to companies anymore, "free plan for a few users and try it out".
Looking at https://tailscale.com/pricing/ one of the other major changes that has been made, is the free plan now provides access to almost every feature. Going up to the $6/mo/use "Starter" plan actually loses you some features. So if you've had a taste of the good life, and want to keep it, but have more than three users… You are going to need to go to the premium or enterprise plans. Probably makes their sales process, super easy, since they don't need to give out trials to companies anymore, "free plan for a few users and try it out".