Hi mjwmott,
I know this was posted a while ago, but I came across poor performance when using osx through m0n0wall to certain sites only.
I turned off rfc 1323 in osx, and seemed to clear the problem.
sudo sysctl -w net.inet.tcp.rfc1323=0
this setting will be lost on reboot of osx, and won't affect existing tcp streams.
I'd be interested if this helps with you problem ?
Thanks