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[Disclaimer: if you're a techie, and you find this discussion a bit patronizing, bear with me. I raise my own salary through donations, and I'm trying to communicate to my non-technical financial supporters where their money is going. If you're one of those supporters, please bear with me when I descend into meaningless jargon.
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Our mail server, which runs Microsoft Exchange, died two weeks ago—critical operating system files got corrupted, and Windows wouldn't boot. This is a bad thing. Bad technically, because it meant reinstalling Windows, which was sure to confuse the Exchange service. Bad corporately, because it took us two days to get mail services back up and running, which meant lots of business not getting done. In point of fact, although we spent several hours with a consultant and a Microsoft engineer, we didn't actually fix the problem; however, we got the mail server back into enough of a working state that business could proceed. So we backed up all our mail and said to ourselves, "don't touch this machine again".
Then I started shopping. Being an intuitive fellow, I listened to that little voice in the back of my head saying, "now would be a good time to outsource our mail". That is, I went looking for someone who could run an Exchange server somewhere else on the Internet for us, and host our mail. If it worked, this would be a big benefit to us because:
Would I have made the same decision if we had 20 users? 100 users? Perhaps. What was more important in my calculations was the ratio of IT workers to other staff. We are right at the point where we need more IT staff, but haven't hired them yet. That is, the demand for IT is outpacing what Ryan and I can supply.
Assume an ideal ratio of 1 IT worker for each 20 staff members. Given our staff of 40 (and growing), if we had 3 IT workers, we might have chosen to keep hosting our own mail. Similarly, if we had 20 staff to our two workers, we would have chosen (and did choose for the past few years) to host our own mail. But because our demand is exceeding our supply, we chose to outsource it for now:

We're still in the process of moving our mail to the new provider, but don't worry about sending us mail! Nothing about that will change. I just wanted to give some of you a peek into the day-to-day (-to-week-to-month?) fires I end up putting out.