I\'m fairly new to both Subversion and Subclipse and am seeing some issues that lead me to believe there is a difference between updating to head, and synchronizing. Specificall
I think your assumption that synchronizing is the same as updating to HEAD is false. If, in Subclipse parlance, "synchronize" means "commit," then it is certainly false because committing does not update your working copy. You have to explicitly update after you commit to be at HEAD.
Which brings me to your second question: I think the reason the bolded line is below other commits is because of the above reason—committing does not update. This means that you can commit a change to a file, and then look at another file and see it as being older than HEAD, because those other files have not also been brought to HEAD.
This article may help clear up this concept of mixed revisions: http://markphip.blogspot.com/2006/12/mixed-revision-working-copies.html
I also encourage you to familiarize yourself with the SVN documentation, as working with plugins and extensions for Subversion always becomes easier when you understand how the underlying SVN system works.