sshuttle does not tunnel UDP out-of-the-box. It only works on Linux and only if you are using the tproxy mode, which is not the default and a little more involved to set up. See: http://sshuttle.readthedocs.io/en/stable/requirements.html#l...
Absolutely not. My colleagues with Macs are using it on macOS just fine.
> a little more involved to set up
Either TPROXY is the default on Arch Linux, or this is false as well. I just installed sshuttle via pacman and it worked without any additional setup.
We (rsync.net) sponsored work to get UDP functionality working with sshuttle on FreeBSD. It is my understanding that it is committed to FreeBSD ... you might need to wait for 11.2 ?