I would generally avoid testing that involves relying on UI elements. I favor integration testing, which tests everything from your database layer up to the view layer (but not the actual layout).
Try to start a test suite before writing a line of actual code in a new project, since it's harder to write tests later.
Choose carefully what you test - don't mindlessly write tests for everything. Sometimes it's a boring task, so don't make it harder. If you write too many tests, you risk abandoning that task under the weight of time-consuming maintenance.
Try to bundle as much functionality as possible into a single test. That way, if something goes wrong, the errors will propagate anyway. For example, if you have a digest-generating class - test the actual output, not every single helper function.
Don't trust yourself. Assume that you will always make mistakes, and so you write tests to make your life easier, not harder.
If you are not feeling good about writing tests, you are probably doing it wrong ;)