[iso1210]

Zero day sshd vulnerability would be bad.

On the other hand if you had to break through wireguard first, and then go through your single well-secured bastion, you'd not only be harder to find, you'd have two layers of protection, and of course you tick the "VPN" box

[lostapathy]

Vpn can also have a zero day, and seems about as likely?

[iso1210]

But if your vpn has a zero day, that lets you get to the ssh server. It's two layers of protection, you'd have to have two zero days to get in instead of one.

You could argue it's overkill, but it's clearly more secure

[lostapathy]

Only if the VPN means you have a VPN and a jump box. If it's "VPN with direct access to several servers and no jump box" there's still only one layer to compromise.