  For the past 3 weeks I've been working with the Wake County Public School System as the Blackboard Administrator for their 4,200 courses and 134,000 user installation. This is a gigantic installation that gets somewhere in the neighborhood of 28,000 hits a day every day of the year including Christmas and New Year. Currently, the version that is installed and supporting those users is Blackboard 5.5.1 which is stable and works well. The problem is that it is really cumbersome to use compared to the latest release 6.1.5. The 5.5.1 system utilizes a WYSIWYG plugin called AOI Systems WYSIWYG. This plugin added functionality that didn't exist in 5.5.1 previously. It was such a great tool that Blackboard purchased it from AOI Systems. Unfortuantely that is where the problem starts. Any content created with the AOI WYSIWYG tool in 5.5.1 is NOT migrating to 6.1!!! When I call Blackboard they claim that it works, which it does not. Then they accused me of being the problem with the migration of the data, which I am not since the migration tool completed successfully. I called AOI Systems and they were aware that the Blackboard migration tool didn't successfully convert the data created with their tool! Essentially Blackboard developers were so singularly focused on their product, they forgot that they bought a plugin that was widely used.
They never created any contingency plans for folks that had created content with the plugin. So rather than fix the problem they are stalling me and saying that it is really my fault that the data migration isn't going smoothly when AOI and I know that their migration tool was coded poorly. This is in addition to all the other support I've required where the answer I've recieved is "Sorry! That isn't documented, but you need to install Hotfix 3..." Or..."Yeah...that didn't make it into the documentation!
You'll need to do X, Y, and Z before that will work. " I don't mean to be ultra critical here, but updating documentation is a key component of reducing help desk calls. Keeping documentation accurate is essential to keeping customers happy. Then when they call blaming them for problems, or admitting that the company did a poor job in documentation only makes the situation worse. It's no wonder that large accounts are going away from Blackboard every year. Michigan State University used to be a huge supporter of Blackboard, but their terrible customer service, ridiculus licensing fee increases, and generally poor instructional design lead them to go with ANGEL.
I am definitely a Blackboard advocate because it is easy to use for end users. However, dealing with them on the management level is a total nightmare. It takes 1 or 2 days to get answers to questions that either shouldn't be asked...or should just take moments to answer. 
