A Small Business nightmare, what would you do?

Ok, I see you're asking yourself the GOOD questions. You're showing passion, engagement, drive. You're seeing a problem, you want to solve that problem. I have a lot of respect for you. But right now you're asking for answer from people who lived through something like that. Experience, something like that. Sometimes, people with experience tend to reject the question if they feel like they are seeing something maybe more relevant to the context than the question itself. So, what I'm going to do is reject your question and tell you to start asking yourself the RIGHT questions. You have been hired to keep something running even if it's terminal, if that were a horse you'd probably need to put it down. Yet you've been tasked to keep it alive. Will it be your fault if it dies? Will it come down to what you did and stain your career ~~if~~ when BitJesus is gonna recall that Data into his green pastures when the server dies? Have you documented what is there, and what WILL happen when it does? Do that first, because you're gonna need the biggest "I told you so" you can muster when people are getting angry at you for not being able to resurrect the monster you're barely keeping alive. And generally (and I mean it with my best intention) [CYA](https://en.wikipedia.org/wiki/Cover_your_ass). It's good to have drive, purpose, meaning. You're going to meet some people who might want to abuse that AND your knowledge (because seriously.. some are thinking we're some kind of mad wizards just because we can open a cmd). Protect your knowledge and respect it by not trying to shoulder something like THAT alone