Colin, I wasn't sure from your reply. Do you mean that you have a license for "Blackboard 9" that will be expiring at the end of this year? One can explore Blackboard Ultra for free, from what I can see from Blackboard's "coursesites" website.
As I read about Blackboard's $1 Billion debt, and see their difficulties, this really makes me think back to "Lotus 1-2-3," the PC-based spreadsheet that probably had about 80% of the spreadsheet market around 1989, or so. What happened to Lotus 1-2-3?
It is easy for companies who have a significant share of a market to get lazy about product improvement and innovation. We all know that Blackboard's historical approach was to purchase competitors, then kill the product. Yep, they always talked about integrating the "best features" from the products that they bought, but this never happened. (WebCT, Angel)
So, my guess is that their debt is due to legal issues, and marketing expenses, but not due to product development (and programmers.)
Time will tell.