Outsource...
There is a good reason SMB's like to keep things in house. Because it works.
We have an IT company that provides support. Right money in fairness and mostly ok. Mostly.
Moved to New PC' s running Windows 7. Our version of sage would not run. Told them to use dosbox (it was an old version of sage, one that HMRC are no longer that acquainted with...) that didn't work. Told them to use the version of dosbox with lpt printer support. Didn't work. Despite me having used the same version for another legacy program that needed to print. But hey ho, I had wanted to upgrade Sage for years anyhow so 600 quid plus a support fee and porting fee later that was sorted.
Email and voip phones are in the cloud. They work most the time. Last outage was actually caused by support company trying to play with the firewall without anyone telling us of this.
Had a few issues with virus, so asked them to sort it and check everything was patched. They said doing such was not in the SLA. Had to point out I had never seen an SLA and that I had specified a totally managed network so it should be done. We don't even have admin accounts or passwords.
Of course every time that we NEED to get hold of them to sort something out, there is no answer from the office. We end up calling every mobile number we have.
All that being said. An entire months support for ten users is a weeks wages for me and you can bet that without their help I would be spending more than one week a month sorting out IT shite... the MD did moan about the cost of it all until I pointed out the cost of 10 x MS office and an in house IT chap on a min of 25k a year.
As with anything in life, the bigger a system is the more open to entropy it is. That's just life.