Strategic planning for migration to open source

I have fired the starting gun on an exercise to create an information pack for schools on open source software. It will have sections on what open source is, a workbook of strategic questions to ask before embarking on a migration, implementation hints and tips a set of case studies (from this site) a directory (again from this site) and questionaire / feedback contacts and so on. The document will be public domain or CC license which is compatible with this site, and I intend to create a "release candidate" for peer scrutiny of this community as I know a lot of you actually work in schools (unlike me).

For me the low growing fruit is in the case studies and software directory that are already documented. I want to take these and cross reference them in the pack based on types of deployment, skills required and a set of other categories. In some cases a school board may have an idea about deploying an open source tool, but no current reference point, hopefully the pack will be able to link a target with a particular case study. On the other side of the coin a school may be looking for ideas but not be aware of their choices, in which case outlines of case studies with references to the full case study would be able to assist. The aim is to make one generic universally accessible pack that puts the case for open source and provides a roadmap to assist getting from concept to implementation.

However what I really need help on is the strategic planning for migration to open source. Ideally I would like to know the kinds of questions that those that have already implemented open source solutions in schools have asked themeselves or (if they were to do it again) would ask themselves before deployment.

I don't work in a school but from my experience of ICT the kinds of questions I would ask as a head or board of governers before making strategic decisions are:

What level of OSS skills do I currently have?

Would the teachers and support staff be willing to migrate?

How can I mitigate the risk of a key staff member leaving?

What will I need to invest in?

These are just 3 that come off the top of my head, I am sure that there are others out there that could think of more. If you could spare the time could you please post your suggestions (and the reasoning behind asking the question)  here so that I may include them in the pack. Similarly if you have any other ideas / suggestions for other sections mentioned (or additional sections) please discuss here.

Thanks for your assistance.