The “wizard” used to join workstations to an SBS 2008 network has undergone some significant changes from the SBS 2003 days. The process is streamlined, it can work with workstations that are domain-joined (including workstations that are joined to the current SBS domain), and it has additional options that were not present in the SBS 2003 version of the wizard. But it still has problems with private profiles, just like its predecessor.
When you go to the new http://connect site, run the tool, and get to the section where you select the local profile to use for the specified domain account, you may find that the profile you want to choose is not listed in the drop-down list. This doesn’t mean that there’s a problem with the profile, just that the profile has probably been marked private.
The simple fix is to open Windows Explorer, browse to C:\Documents and Settings, right-click on the user’s folder, and clear the “Make Folder Private” checkbox. Apply the changes, close the window, and run the Connect Computer tool again. The profile should show in the list now. If it still does not, go back into the folder settings, enable the “Make Folder Private” checkbox, apply the changes, then disable the “Make Folder Private” checkbox and apply the changes again.