The iTwin ($99, www.itwin.com) is a handy way to securely share files with no worries about logins or fiddling with settings. Using a familiar drag-and-drop model that anyone who’s used a USB thumb drive can understand, the iTwin just works. And you can get one if you win our August contest.
Moving files: You have a lot of choices, and they all have drawbacks. Emailing files gets unwieldy when you make a lot of changes, and some people worry about the security of cloud services like Dropbox. You can set up file sharing in System Preferences > Sharing, but it can be a confusing process for beginning users, especially using it cross-platform. iTwin combines the ease of using a USB thumb drive with the seemingly magical convenience of file sharing—the company wants you to think of it “like a transfer cable without the cable,” and that’s pretty much how it works.