I think you answered the question. Sugar. It's easier than managing your own Wireguard connections. Adding a device just means logging into the Tailscale client, no need to distribute information to or from other devices. Get a new phone while traveling because yours was stolen? You can set up Tailscale and be back on your private network in a couple minutes.
Why did people use Dropbox instead of setting up their own FTP servers? Because it was easier.
Yeah, but "people" here are alleged software engieners. It is quite disheartening.