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because it's not hip anymore. This is for the beardy old unix guys who don't understand the whole new world in the clouds.

Perhaps it has one S too many.

Because SSH might be blocked, and not only trough port 22 blocking but firewalls sniffing traffic and blocking on OpenSSH in the connection (eg. SSH-2.0-OpenSSH_8.1).

Then this stuff would also be blocked for the exact same reason. And if it isn't, you will probably be fired for knowingly and willfully circumventing security measures.

I have gotten around this by hosting SSHD on web ports before, or going through a SOCKS proxy.

You might be on a hostile, locked down client, on a hostile network. This lets you access a *nix machine you control from no more than an internet kiosk at a hotel.

I definitely would not want to use a hostile machine to access my servers remotely, period. Sure, this will let you bypass outbound port restrictions, but it doesn't help in the slightest if every keystroke is keylogged.

Keystrokes being logged could be avoided with 2FA plus not typing in sensitive content.

That doesn't secure you against MITM from the machines. E.g. if the machine is taken over locally or remotely or there's spyware running on it, you could still end up compromised.

(I'm not saying you should do this; you probably shouldn't.)