I've had some sort of handheld PDA since 1995, and have long had to back up all that data to my main desktop computer. But a while ago I bought a T-Mobile HTC G1 Android phone, and while it still seems a little buggy, it's been amazing because now, for the first time, I've been able to move all my data into the "cloud", and access it continuously from anywhere. And so, while I'm still fanatical about backing everything up, the days of tediously syncing an online calendar with my PDA with my home PC with my laptop are gone. I got my 500 or so active contacts synced to the GMail address book last week, and today, I finally finished moving my recent calendar archive into Google calendars (which was a painful process because they have an undocumented daily data event import quota of 5,000 events). And so now, from my phone or from home or from work, I have access to all my contacts and my calendar data back to the year 2000 (which is great because I have a terrible memory for what happened which year (What year did I paddle in Newfoundland? When was I working on the Elvis show tour? I have no idea.)). Today I found a way to convert my calendars from the 1990's, so I'm going to take a stab at getting that data imported next. And I'll tackle the 80's after that.
While the transition has cost me a lot of time, buying the G1 has actually saved me time on a day to day basis and it's not often that I can say that about any new technology!