I would like a Win machine to tunnel into an SSH server whenever the machine starts up. I also want the win machine to reboot the SSH program if it ever crashes. The lighterweight & more stable the SSH program, the more happier I am.
What options do I have with this?
The PuTTY suite is probably your best bet, IMO. (Disclaimer: I'm biased as Simon Tatham is a friend of mine from university. Mind you, that means I know how meticulous he is...)
Look at using srvany to launch the SSH client as a windows service. Then you can set the service to start up automatically when Windows start.
Essentially, srvany.exe will let you launch any program from the windows service control manager.