When it comes to personal information like email, calendars, to- do's and notes, I have super systems that keep all the data up-to-date by leveraging the cloud and keeping local copies on my computers and my iPhone. Evernote, for example, is one great tool that I use to stay in sync.
Contact information, on the other hand, has always been a pain.
The basic tools like the address book that comes with your computer are outdated. People move around too much these days. Enter social networking. The problem is keeping your information in sync everywhere.
The new version of Facebook for the iPhone, however, at least for me is finally
a workable solution because it has an integrated dialer. Part of the reason it works is because I limit my Facebook friends only to those whom I have met or corresponded.
Like Robert Scoble, I wish that people would add their phone numbers to their Facebook accounts so that this becomes the ultimate solution. It sounds like soon Facebook will
keep your contact information in sync, which will make this all easier. However, all of this depends on if people keep their contact info current - which isn't a given because of privacy concerns.