What are you trying to do?

It looks like the Tailscale Homebrew formula¹ works pretty well on macOS (on both x86_64 and arm64).

Specifically, the following steps seem to be sufficient to install Tailscale and run it in the background (and Tailscale will start up at system boot, before any user has logged in):

# do NOT use `sudo` in this first step:
brew install --formula tailscale

# for these next three command, you need to have the `sudo`:
sudo brew services start tailscale
sudo tailscale up
sudo tailscale status

Would it be possible to mention Homebrew as an option in the Tailscaled-on-macOS wiki page?

If necessary, maybe you could include some kind of disclaimer in the Homebrew section, e.g. something like:

Please note that Tailscale Inc. does not maintain the Homebrew formula for Tailscale.

How should we solve this?

By adding the instructions (for installing the Tailscale Homebrew formula on macOS) to the "Tailscaled on macOS" wiki page.

What is the impact of not solving this?

Users will need to read through various GitHub issues in order to be able to figure out how to install Tailscale in Homebrew.

Anything else?

Cross-ref #177

Cross-ref #987 (by running the Homebrew service under sudo, Tailscale will be run as the system, and will start up at system boot, etc.)