I was getting very frustrated with Retrospect not launching automatically in 10.2 Turning on the console confirms that retrorun crashes everytime it tries to launch. I thought I was doing something wrong, but after checking the Dantz website, it turns out that this is a known bug.
The workaround is simple. Use Cronnix (freeware) to create a crontab that launches Retrospect at a specified time. Here is an example of my cron entry for Retrospect:
Min 0 Hour 1 MDay * Month * WDay *Note: shown on three lines, needs to be one line ... this launches Retrospect every day at 1:00AM, which is perfect since my backup script launches at 2:00AM.
Command /usr/bin/open "/Applications/Utilities/
Retrospect 5.0/Retrospect"
Mac OS X Hints
http://hints.macworld.com/article.php?story=20020925061104858