PC enthusiasts never seem to have a problem sending files back and forth over the Internet. There are plenty of different methods to use, and at least one of 'em will probably work for the person on the other end of the transfer. The thing is, transferring files isn't all that straightforward without additional software or the assistance of third-party websites. Unless the file to be sent is under the attachment size threshold of both parties' email accounts, mainstream users don't stand much of a chance of figuring things out without a call to whichever friend of family member they have on speed dial for tech support.
XKCD summed up the situation nicely a couple of weeks ago, and I just stumbled upon what looks like a novel solution while cruising Wired's Gadget Lab blog. A company called iTwin has developed a two-headed USB dongle that, with the assistance of software, allows files to be transferred wirelessly between computers that have one half of the device plugged in. The system guards the virtual connection between iTwin halves with 256-bit AES encryption, and one can set a password on top of that for additional peace of mind. Users can also disable the other half of a pair remotely if it's lost or stolen.
With a $100 street price, the iTwin is an expensive alternative to the free methods most of us use on a daily basis—ones that don't require specialized hardware. The iTwin might be easier to explain to your mother, but it also needs one half of the dongle to be present at both ends of the transfer. The fact that such a product exists at all underscores just how complicated something as simple as sending files over the Internet can be.