I wish you were right. In my line of business it seems like all the dorks of the world collided in the development department, but none of them understood the industry, nor cared to ask the future buyers. But since the entrance toll is very high the buyers (us) don't really have options. We picked the least bad software/service provider. That doesn't mean we are happy with what we are served. For this reason alone I consider the work-groups of stakeholders gathered from each buyer to be vastly superior in expertise. The designers of our software tools are not. And they prove it every time we meet and for every new tool they build.

Which brings me to: Yes, it should always be considered which is the least expensive: To change the off-the-shelf software (or build your own!), or to change the habits of employees, or the employees altogether.
It is just that I have realized that we will never buy a piece of software if it doesn't fit the way we are already working... simply because the ones doing the decision making in this buying process doesn't like to get their habits and laziness challenged.