I'll keep this brief.  I need to get back to bashing my head against a brick wall.
I am in the process up upgrading to a new laptop.  I have transferred Skype, Outlook and Firefox over to a new machine.
1) Skype - decentralised storage of contacts, so just install and log onto new machine and you are up and running, EXCEPT you don't get the chat history.  The help isn't helpful as it tells you where the history is stored and how to back it up, but not how to transfer it to a new machine - that would be too easy!
2) Outlook - Three documents to read, backup, moving your pst and where files live.  None of them complete the process of how to move all you e-mails and settings over to a new machine with the same version of Outlook on it.  So I skip backup, and just move all the files to the same location on the new machine.  I was expecting it all to blow up, but it seems to work.  Layouts have gone back to defaults and not sure what it has moved over other than my messages.
3) Firefox - help tells you where all the files are, you just copy them over to the appropriate place on the new machine and you get everything, history, searches, plugins, skins, the lot.

Moral of the story, why do developers make things so complicated for themselves and users.  Next onto moving Delphi 7 and another dozen -> 20 programs.  wish me luck!