It sounds like mainly he's saying he is done with Windows and MS Office. Definitely the trend these days, and it's good to see someone who is tech savvy but not a techie going down that path. A MacBook Pro and an iMac are still traditional 'desktop' devices, though. I guess the key is that he's ditching the desktop software stack in favor of the new mobile era style software and cloud storage.
Myself, I moved all my vital email, coding, and business administration from a desktop box with Linux to an Android phone and an MBP on the last trip I took. When I came back, I didn't bother switching back. however, I'm not ready to abandon the safety of my own hard drive.
Ah, life in the US - really, the FBI could kick down my door and take all my computing equipment for any or no reason at any time. Grumbling about Twitter or Amazon is about as controversial as I get, though. Is it better to have your data stored in 'the cloud'? Not really. It's vital have encrypted backups here and there one way or the other.
The door kicking and the border scenario are different. With the door kicking you had to first be noticed by the FBI, but with the border crossing you're placing yourself under the gov's arbitrary notice. Both scenarios are unlikely. Unless you're controversial, or you happen to get a border guard on your or their bad day.
I know police have been looking through mobile phones at traffic stops for a few years at least, too, and now some even have device which will copy the entire contents of the phone for later analysis. Traffic stops can be pretty casual.
I'm wondering, though, are you saying I should be concerned about losing the hardware or the data in particular? You mean, store everything in the cloud so access to my hardware doesn't automatically mean access to my data? How about TrueCrypt or Apple's encrypted home partition option?
Definitely. An even more likely scenario for someone as fritter-headed as I can be is that I'll leave it at a coffee shop or hotel, no outside malice required! Definitely a big concern for mobile devices, and I've been thinking lately about how crucial this makes my MBP. It's definitely not as safe as the system at my house.
What I used to do is have everything on my home system, then connect to it through VNC or NX from the road. It's great when there's a fast connection available, but too frequently VNC is unusable due to unreliable internet connections. I'll get this network thing figured out some day.
You could via ssh, but it's not comfortable due to the screen size. I picked a phone with a physical keyboard, which helps a lot. I've used my phone to fix code and restart servers, and I love that the possibility is there in case of emergency.