We use Basecamp for our project management, and we often get asked how we like to have To-Do items entered. Often we find that people put the entire text of the bug or action item in what is intended to be the item title. They miss the ability to add comments - and thus, the ability to attach files, since files are attached to comments. We've put together a quick (one minute) demo on what we consider to be "best practice" for adding To Do items:
Hope that helps!