It would depend on how well the prison is ran.
Often the jails are just filled with drug offenders. Not the harden criminals. For a nerd it would be like being at high school again.
However many IT Guys are just as big and tough as any other person who goes into prison. This is 2016 not the 1980's Revenge of the Nerds movies.
Well it was done on the guys personal time. It may had made sense to not to try to get too greedy. If he needed to hire an outside contractor to do the work, over $100.00 is not unreasonable. However most companies who have to do the random residential fix, usually tries to cut them some slack and do the work at cost, as to not garner bad reviews.
Now this is actually a tricky concept. The GNU People think software should be owned by anyone with. While most companies who make their money writing software wants controls on what is happening so they can support and make money off it.
Then you get to the problem where these systems are all hooked up to a network and are communicating with other systems. Where we need to be sure that we get constant updates to these systems otherwise we will be part of a problem of creating more insecure networks and makes it easier for malware and hacks to become really common.
You could use the same argument that is used for Vaccines, that you should be forced to update as to help keep the overall network secure and operational. However unlike vaccines, there are good reasons to not upgrading. Mostly due to backwards compatibility issues that occur, and for the case of going from Windows 7 to Windows 10 switching to an interface that is dramatically different and not necessarily optimized for your work.
If we were to own our software again... We will need to be responsible for any problems that we may cause to the outside public. And most people are just not savvy enough to do this.
I have a very small mind and must live with it. -- E. Dijkstra