Thanks for posting this discussion. I wasn't able to make the live session but I listened to the recording.
I have a question. It certainly sounds complicated keeping track of all of the license issues with proprietary software. I was wondering why you did not mention free open source software licenses which do not have any of the issues that you discussed. There is a lot of software suitable for non-profits that use the free open source license.
One simple easy thing that most non-profits can do is to replace Microsoft Office with the free OpenOffice.org software. This can be freely installed on as many computers as desired with none of the licensing issues of Microsoft Office.
There are free open source software packages that can replace most of the proprietary packages that you mentioned in your session. These can all be freely installed and used without needing to buy and track licenses.
Linux can replace Windows XP, Vista and Microsoft Server software with no need to buy or track licenses. Linux also does not have any viruses, trojans, or other malware due to it's better security design.
The story you told about a non-profit that was audited by Microsoft and had to pay a big fine due to lax license management should be a warning to everyone. Free open source software does not have this issue.
You also mentioned that most purchased software does not come with support. Free open source software has many avenues of support both free and paid. I have found that it is much easier to find answers to open source software questions than most of the proprietary packages.