I don't know the condition which triggers the import settings dialog short of a reinstall
There is a difference between Safe Mode and Re-personalization. Safe mode is invoked by holding the SHIFT key will opening a project.
Re-personalization is not the same as importing setup information from a previous version
There are two levels of re-personalization,
1) Holding the SHIFT key while opening SONAR - causes SONAR to replace any files which are missing from the user directory from the master copy ProgramData.
2) Holding the CTRL+SHIFT keys while opening SONAR - causes SONAR to overwrite the files in the user directory with the master copy in ProgramData and resets some registry entries.
FWIW, Noel recommends against importing previous setup information see
http://forum.cakewalk.com/FindPost/3031243 and his follow up post below it.