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Data exchange - good question!
Data exchange is a sticky issue for today, but is getting much better as time goes on. Yes, the broadcast-happy nature of windoze is not good for networks, but is perfect for a rapidly changing environment such as wearables.
Something that's designed more like the irda data exchange interface of win95 would be better suited. open one app/window, and you can drag and drop files into it and they'll automatically be transmitted. secondary-click on a file from the file browser and one of the menu items should be "send via ir" or something like that.
This is good for exchanging medium to large amounts of data when the content is dynamically determined, i.e. spontaneous query for non-static data.
On the other hand, if you have small quantities of data (business card, contact information, url reference), something like the javabutton would be perfect! Carry a dozen of them in your wallet and you can hand off your data in about 3-5 seconds. Business card may be a bit too big, but you get the idea - something small, light, highly durable.
Most importantly, these things need to be CHEAP. Business cards are cheap, so I have no qualms about throwing out half a dozen of them as coasters when I need to. any sort of flash memory, though will cost a few bucks, and until people are willing to get over the mindset of "this is costing me something - I don't want to *give* it away", data exchange will not become as pervasive and simple as that.
So, as people mentioned, there are several ways you can go about data exchange today:
Preconfigure ppp, pppd, and spend the 10-15 minutes to use a null modem cable and the serial port. "dial into" the wearable, ftp your data.
zmodem directly over the serial line, and hope that the pc has comm software installed
dhcp_bootp, and temporarily disconnect the pc from the existing network to form a temporary network with your wearable. Only usable in non-NT Domain situations. Only usable with a networked pc.
irda - pretty much only good with laptops, and irda support on linux isn't that good.
Every approach has its problems, the fundamental problem being does the computer you're trying to talk to have the matching software you need? With Mr Murphy ruling our lives, the answer is probably no. Until networking becomes as ubiquitous as we want it to be (unix *has* had ubiquitous networking, but only for static configs, so I consider myself spoiled), we will continue to have these sorts of problems.
Me, I have a script that configures my laptop for generic dhcp client, ppp connection through my ricochet. The generic dhcp client configuration works for me at work, at home, and other places that I've insured that the network services I need (dhcp server) are present. It took some work to get it all right, but it does makes my daily life pretty easy; just one command connects me to most boxes. Eventually, I want to make a script that will automatically detect my location and configure itself automagically. i.e. probe for the ricochet and if it's connected and on, automatically dial.