This story brings back a lot of memories. Right before I separated from the USAF in 1997, I was working with a tanker squadron deployed in support of operations in Bosnia. Crews would spend hours parsing the Air Tasking Orders to figure out when to take off, and with how much fuel. I had just gotten in to programming and wrote a simple VB6 app to parse the huge file and produce a simple report with the details they were after. It saved the crews hours, and I was still getting feature requests on the app for a year after I separated. It's simply amazing it took another 20 years for them to solve the problem.
There is an, unfortunate, lack of continuity in many offices like that in the military. This is due (as you're aware, this statement is more for others) to the way that personnel get moved within the military. Officers, in particular, as the ones who are typically the "decision makers" for selecting what projects to work on will be in their job for 2-3 years at a time. If they don't have a chief or a civilian staffer who acts as a continuity officer, projects like what you did get forgotten.
"Why are we still using this VB6 thing after 15 years? We should put out a contract and have it done properly." says some colonel or major who doesn't know better. And so it happens, a contract is awarded and it's a mess. I saw it more from the civilian side. Without strong continuity officers, when the military leadership changed over the direction and intent of things is forgotten.
Additionally, as this article points out, the military is set on Waterfall-styled contracts and projects, given to the lowest bidders. Which is why it becomes a mess once a contract is awarded. Waterfall only works under a few circumstances, and I guarantee your lowest bidder won't satisfy them all (expertise with the implementation technology, expertise in the problem domain, expertise with how the system is actually used, ideally a project that's been done 100x before by the same team).
