From Dave Noon, "Christ, I hate Blackboard", Lawyers, Guns & Money 1/24/2014:
Hundreds of years from now, after disease and fire and famine have thinned the human herd to a shrunken patchwork of sagging, skeletal bands of jagged, half-mad wraiths — when the parched soil chokes forth desiccated roots and the air is a toxic brume slumping down on the arched, knotted backs of the still-barely-living — a remote spur of humanity will somehow recover the capacity to speak, an ability long since abandoned by their ancestors, who were mute-struck with the unfathomable despair of those cursed to watch everything they love die. After generations of dry-throated croaking and lung-starched wheezing, their tongues swollen with thirst and punctured with abscesses that never heal, these distant people will bring forth a new language to survey the boundaries of their pain. [...]
On the outskirts of this new language, lurking on its crimsoned frontier, will lie words that will themselves have been cast into exile – foul offgassings within a lexicon that itself stands as a towering monument to the boundlessly obscene, words that will curve backward and devour themselves, each one an afflicted universe in the process of total collapse, words that exist for microseconds before streaking, unremembered and unmourned, into the void.
These are the words, if I could shit them into being, that I would use to catalogue the depth of my loathing for Blackboard.
You should definitely read the whole thing.
Why are certain types of software systems so reliably bad? In my understanding, it's a combination of the process of specification and implementation, the (mis-)education and general outlook of the designers and implementers, and the characteristics that the people in charge are actually trying to optimize.
We've commented on some of these issues from time to time in the past, e.g. "If you can answer this, you are not paying attention", 7/10/2006, or "When bad interaction happens to good people", 8/15/2007. (That last post dealt with a system for which I wrote a tongue-in-cheek-but-serious Users Guide, "The Legend of FacilityFocus". The software has since been improved in ways that make it substantially easier to navigate, though there are still difficulties due to things like systematic differences between floor numbering in the master database and floor numbering as marked on the building signage…)
I tried using Blackboard once, many years ago when my institution first switched to it. I gave up for two reasons: it was an order of magnitude harder than just putting stuff up on the web; and all the stuff I painfully entered in it vanished from one year to the next, on purpose but without warning. Penn has now switched to Canvas, which I haven't yet tried.
I do use Piazza, and generally find it well designed and helpful — I suspect that this is because it came out of a different sort of development process.