Well, first, I have been lucky to get incredibly good online support in Networking, SQL and Hardware by going to Experts-Exchange. I have 505 posts there and have met some great IT people whom I trust explicitly.
As far as finding IT people, it's the same as finding a good MA or a good contractor. You have to work at it and use word of mouth. My point is not that Dell or Microsoft can fix AC, they are an example of good, dependable IT that will cost some money. The issue is, it isn't usually AC as too many people on here are way too quick to jump to, it is their server, their main computer, their network. As Rob (network person) always tells me (in my domain environment), it is DNS, DNS, DNS. Not AC, AC. We need AC support for glitches in AC. Dr. West needed It who could fix his printer and scanner, neither of which had anything to do with AC, but according to him, resulted in a lot of downtime.
I think if you found a company, not a 23 year old solo IT person, who specialized in Microsoft and were Microsoft-certified with all the credentialing, they would be your IT. They would come out and look at your network. They would start at your modem, go to your router/firewall, look at your switch, follow the cables to your RJ-45 jacks, checkout the NIC cards and use a fluke meter to test all connections and connection speed. They would then know your system is set up correctly and, more importantly, they would know your system, just like you know Mrs. Jones and her thyroid issues. You would be able to call them after hours (for an extra fee), they would promise in the contract to answer the phone or send out a tech that day.
As to your final statement, I have often wondered about how great that would be. It would be like Firefox and, actually, like my three programs where Ed just adds a new update to the web. The next time you open F.A.P. or Firefox, you are told an update is available. I trust Ed. I certainly trust Firefox. I just assume that both have updates that improve the product. These also must use one-click web installs, which AC does not use.
The issue would be exempliefied by, ironically, you and me. Neither of us have jumped to 6.09. Why? Because of ePrescribe among other things. I just wouldn't be all set to update the program that way. And, I would have to trust all of my users to do the same (again where GPO on a server would be useful). Going backwards is not fun with AC.