Tricky? Uhhhh, yeah! Very perplexing....
You seem to have a lot of services open -- I'm wondering might there be a conflict. Two things I would suggest trying would be (1) turn off (temporarily) all services but ssh and ARD-enabled VNC, as in shut down those services on the firewall and making sure that your programs like FileMaker, etc., aren't running as faceless daemons in the background, and (2) try setting this up in the reverse direction with your iMac as the local VNC client connecting to your Powerbook as the VNC server.
A couple of other things -- you don't have any copies of Apple Remote Desktop client installed and/or running anywhere, do you (other than the "OEM" configuration of ARD in the firewall settings of your system preferences' sharing stuff)? I don't have ARD client (it's like big buck$ so I find CotVNC's quite adequate on a feature-to-cost ratio basis), but I'm wondering that since ARD client is, as I understand it, VNC-like, whether there might be some sort of conflict going on with that and CotVNC. There wouldn't be some esoteric setting in VNC about a password to control the screen or something like that, that is somehow, through some configuration file buried in the bowels of your computers, conflicting with what you are trying to do here? Seems unlikely, but, right now it sounds like your ssh/ARD-enabled-VNC config is identical to both instances of mine so I'm really perplexed as to why mine work and yours don't.
I had asked earlier about when your iBook is inside your work's firewall, and you said that when you connected VNC to your iBook specifying the iMac's IP address as the CotVNC host address, that that worked okay, right? While inside the firewall, and setting up a ssh tunnel, you still crash and burn, right?
Also, since you have personal file sharing enabled on your iMac, are you (as I successfully do) tunneling that in ssh so you can securely afp-mount your iMac on your iBook? I do that with a
-L 5480:localhost:548 port tunneling directive in my ssh login command, and then in the Finder, I
⌘k to afp-mount
localhost:5480. Does that work for you? I'm just trying to see if other services seem to be tunneling okay for you.