I deal with a fair bit of customers like this (not via my business), enough that firing them all isn’t an option because it’s a large portion of the market where I am. It’s something. They’ll have low end servers with no redundancy, terrible or no backups, and no contingency plans for anything. They won’t spend a nickel and are the most likely to lose their minds if anything goes wrong.
This is why services like Google Apps or managed exchange hosting exist. Most people are terrible at IT management. So bad they're far, far from realizing how bad they even are.
When you consider you're getting like 1000 of the smartest tech people in the world to manage your infrastructure for you, for $5/month per user, it's really such a no-brainer. If people are too stubborn to see that, or want to waste time trying to do it better themselves "because it's cheaper", with redundant power, OS patching, zero-downtime changes/deploys, proper capacity planning, proper redundant connectivity, provisioning the right network around it, physically securing the server room, ensuring things are properly cooled, not wet...I could go on forever, and this isn't even the main focus of the business...I'm sorry, but they deserve go to out of business.
I had a very stubborn client once who ran a hotel chain. Won't say what or where, but I wasn't surprised when their random "security through obscurity" VNC server got compromised. I wasn't finishing migrating to the new PCI-DSS compliant system we built, either, so there go 5000 credit cards "encrypted" with some sweet rot13-level bullshit in Turbo Pascal I cracked in about 30 minutes with no code access.
Seems like some dedicated hardware here would make this go faster if there's a business for it. For example, if the bandwidth isn't high, you could setup a wireless mesh from point A to point B and connect via some appliance to the NIC.
Walk the length with the appliance and verify there's no dead spots, then just hook up to a power supply and get things done.
It’s so frustrating and stressful.