I'd love to just sync everything automatically. Unfortunately, in the real world we still have serious limitations. For example, my work database (marketing) may be tens or hundreds of thousands of prospects. I have more than 15,000 followers on Twitter alone. If I attempted to become a tad more intimate with that audience, I'd have a massive contact sheet for a portable device. Tools like Gmail, Thunderbird, Outlook, etc. are much more tolerant to such heft. And, I realize most folks don't have anywhere near that need. So, I'll address the two separate issues as just that - separate issues. 1) We need a sync tool that makes our social media and free services talk to our commercial or personal software incarnations so that we know when we're suppose to be somewhere, with whom we're meeting, if they RSVP'd if requested and a host of other seemingly simple social requisites that get quite messy as we try to merge them into all our daily tools and tasks.

Compiling vs. Merging

Likely the largest hassle we've got with our free services (like Gmail) is multiple entries for the same person. Formatting all this data into some logical order isn't as simple as one may think. We have aging technologies that had extremely simple goals when they were introduced to us. Now we find ourselves hopeful that the services may actually simplify our lives more than just help us send someone an email. Most utilities simply add the duplicate contacts with their conflicting contact information (depending on when we last updated that information). Since many of our contacts are automatically gleaned from email, we often have many contacts we've never verified. Compounding the problem, tools often leave out important fields of information, like addresses and phone numbers. How do we make it all work?

Calendars

Calendars pose their own set of challenges. Mostly the challenge here is different methods of doing the same things. For example, the process with an Outlook/Exchange group is fairly well regulated, but the way Facebook handles an event is slightly different. Syncing all these things is a big and complex challenge if not left to the most basic of "here's what I'm doing and when."