Nov  7 01:09:20 mail pflogd[350]: [priv]: msg PRIV_OPEN_LOG received
Nov  7 01:09:58 mail Enabling pf.
Nov  7 01:09:58 mail no IP address found for tun0
Nov  7 01:09:58 mail /etc/pf.conf:23:
Nov  7 01:09:58 mail could not parse host specification
Nov  7 01:09:58 mail 
Nov  7 01:09:58 mail pfctl:
Nov  7 01:09:58 mail Syntax error in config file: pf rules not loaded
Nov  7 01:09:58 mail
Nov  7 01:09:58 mail pf enabled

the pf.conf rule on line 23:
nat on $tun_if from $desktop to any -> $tun_if

because the tun0 doesn't quite have its IP yet, it appears to just ignore pf and continue with init.