1. Once you work for a big bureaucracy, you realize how slow this stuff is. In terms of how much actual work it takes, it depends very much on the condition of the test environment -- whether it has been maintained and how much effort is required to get back up and running. Plus, how much paperwork is involved in dealing with the government agency that contracts this out. I can easily see a situation in which you don't even accept jobs that are less than 2000 hours as it's not worth it.
2. What I described is not the actual fix, it is the temporary stopgap. The prison department isn't going to pay someone to click checkboxes all the time for tens of thousands of inmates each year. They will want this info to be set automatically -- e.g. an integration from whatever software system(s) are used to track completion of the coursework to this system, so you are not hiring another employee to sit and click all the time nor do you need to create reporting procedures to get that info into the hands of the person who is clicking. The appropriate design then requires automation, which will require security controls, and it's a pain. It could easily be more than a year of work, again depending on how many systems they need to integrate against, what types of sign off/controls are required, how much paperwork is required, etc.
For example, maybe the coursework has no software tracking, in which case they need to throw up a portal and have the people running the course fill out who did what, and then throw up another portal to have someone else review that.
Lots of stuff ends up being passed around by ftp or csv uploads. I've seen horror stories. So it really depends on how they plan to do this integration -- the manual button clicking was just an example of a least effort system that relied on a lot of manual labor, but perhaps this is not in their budget either.