Heck, even within my niche corner of the enterprise world (coincidentally a similar niche as Blackboard), there's always a noisy client who demands X. I can make all the good-faith arguments about why X really isn't needed, but if that client is threatening to go to a different vendor or sue, X is getting built. As a developer, there's only so much I can do before an account executive or C-suite tells me to quite bitching and just do it (and more often than not, they don't disagree with me in principle, but money makes the world go around).

Despite what it seems, demand for features is really NOT why enterprise software is (so often) bad. The problem is how easy it is to SELL fundamentally bad software simply because you can tick a box saying it has the feature.

Yes, I too have seen the phenomenon of having too many people demanding features where the result turns out to be an incoherent mess. But I also know that if the massive amount of time and money that had been spent purchasing a box-ticking Enterprise Software Solution and subsequently hammering the awkward, unwieldy platform into some semblance of working order had been spent instead on direct improvements to the existing workflow software, then everyone would have been much more satisfied. And yeah I know I shouldn't speak hypothetically but you'll just have to decide to trust me on this or not.

I think you're absolutely right. One error some organizations make is trying to buy a COTS product they assume will be simpler and more robust (and have its bugs fixed "for free" by the developer of the product) over hiring a part-time or full-time staffer to maintain and improve their existing non-COTS workflow (including owning all the bugs).

Sometimes (I have no global numbers to even guess at how often), they end up discovering that the COTS product requires expert-level configuration and administration anyway and now they're footing the bill for someone else's licensed solution and a staffer to understand it and make it work.

They aren't, though. If the big "Enterprise Software" players like Salesforce and SAP sell to healthcare providers it's either not with their flagship products, or else it's with incidental business processes not related to their core and peculiar requirements.