[Hizonner]

That stuff fundamentally does not work against anybody with enough of a clue to be playing tunneling games (or using ssh) in the first place. If you have any significant control over both ends of the connection, then it's trivial to obfuscate anything you want so that the firewall can't detect it.

... and those boxes, all of them, have a really bad history of security bugs themselves.

The risks you're taking by undermining the cryptography and putting random unnecessary devices in positions of trust are almost always greater than the risks you mitigate. What you're really buying with those devices is the illusion of control and/or the ability to claim you "tried".