I just upgraded an SBS2003 to sbs2008, it went pretty smooth. One of the issues I have after the fact is the one Windows 7 user. We have the "(my) documents" folder redirected to the personal drive of the users, after the migration, his my pictures folder shows "my pictures" from his pc to his personal drive, but the folder on the server is the vista/windows7 "pictures" folder. All the data is still there, but I can't get his account to "see" the pictures folder.
I've recreated all the GPO's that deal with folder redirection. New logon scripts. I've verified his settings in AD. We aren't using DFS paths or anything different, just regular shares. he has full permissions on the share and in ntfs.. etc etc.
the only thing I haven't done is recreate his roaming profile. He is the CEO of the company and He finally got his machine working the way he wants, so I don't want to have to put him through a profile rebuild if possible. I am granting 500 points as I can't find anything in TechNet or Google, and a verified "seen this, do this answer" will get all the points. No "did you reboot" suggestions please.