So I made some changes such as switching to open source software that can also run from the drive (portableapps.com) so I didn't need any install cd's and when I was shopping for a new computer bought the smallest lightest laptop I cold afford (at 3.5lbs its not much more heavy than an external drive). With the laptop if I need to bug out I take it and can start working in any place I stop at be it my bug out location or hotel without needing to find something to plug my drive in to. I actually have an old HP portable printer in my long term gear for if I would need that now as well, I picked it up for $5.
I can't say enough good stuff aout Portableapps.com
I've been keeping in touch with John Haller, the mastermind behind the site, since the very first release of Portable Apps.
Even better is to use OpenOffice.org (called Neooffice on the Mac). This is the only 100% cross-platform fully functional office application there is. (Openoffice portable edition will run from a USB stick or external drive just fine).
The most important thing you need to do with your data is SYNCH it with as many storage tools as you can. I am a big user of Google Docs especially with their Synch tools.