GSuite is easy to justify for me. Github is. JIRA is. Tailscale is more expensive than all of them and it's hard for me to make the case, even to myself, that it's worth it.
I'd like to ask Tailscale to think about alternative pricing models of maybe $20/month per admin account, which comes with 10 bundled "member" accounts or similar. That would get me to $40 or $60 a month, which I can stomach. But I won't pay $300+/month to save myself a little bit of inconvenience every few weeks so my devs can securely log into our servers.