Usually these drives will be mounted on Linux. But occasionally they will be mounted on Windows 10 where I do not have admin or developer mode access, so I cannot depend on symlinks.

Thanks for the wise words. However I have some questions:

If you’re worried about someone malicious having access to your network connection, ssh is going to do a DNS lookup to map the hostname to an IP for the client.

Are you sure that this is true for Tor? .onion addresses never resolve to an IP address, even for the end user client. If I was on an untrusted network, both for the client and the server, the attacker could find out that I was using Tor, but not know literally anything more than that.

And attackers have aimed to exploit things like buffer overflows in IDSes before – this is a real thing.

I would expect an IDS to be an order of magnitude larger attack surface than Wireguard, and significantly less tested. Although I could also say that about SSH, and we had the recent backdoor. However, I think it is a lot more likely that a bug will cause a security method to be ineffective than actively turn it in to a method for exfiltration or remote access though. For example, with the recent SSH backdoor, if those servers had protected SSH behind Wireguard then they would have been safe even if SSH was compromised.