Ohhhkay so I've found a way around this little problem :D I've found that if I use systray2-lsbox, and load it with a *WharfModule instead of a *NetLoadModule and a !hook, it works perfectly 100% of the time. Hot dog!

Still, it'd be nice to have a !SystrayWaitForBoxHook command to make it so we can use the most recent release and still be able to have a hooked auto-sizing, auto-box-sizing systray ;)

I officially pronounce this problem solved.