User Interface: Cut out the Cruft
Drupal does a lot of things very well, but right out of the box it can put users through a pretty dramatic learning curve. Creating content, jargon-y controls, and other little things will give users who are uncomfortable at the computer palpitations. I've learned the hard way that I always need to be looking for ways to take the confusion out of the interface for my users. The simpler I can make the forms, the more likely my users are to be able to use them.
One of my favorite ways to do that is with the Better Formats module. Because, let's face it, the "help" information under a text area on the node creation form -- the one that shows the allowed html tags, etc -- these uncomfortable users will look at that sort of stuff and get spooked pretty quickly.
Better Formats allows you to elect not to display that information to users based on rolls. In that way, you can give stronger users the information they need to interact with the site in a effective way, while hiding that sort of complexity from the users who won't know what to do with the information.
What sort of UI tricks do YOU use to keep your low-tech users from having a hairy freakout?