Hope he is demanding an obscene salary also, given he is the only thing keeping that server running. I wouldn't do it for less than 300k/yr, probably closer to 400k.

The cloud is a scam, its just someone else's computer. If you're a smallish company you're going to be better off in the long run investing in your own hardware and some well paid people that can maintain it. At a certain point it gets harder to scale, but at that point you'll be rolling in the dough if you played your cards right.