The most important requirement is that any group wanting front page exposure must have a representative who creates that article on the website to begin with. The website team does not create articles for groups that want publicity, as much as we might sympathize with that need, but we will happily train any who are willing to learn to post their own.
The second criteria is that in almost every case there should be some sort of illustration. A photo or two adds interest and color to any article. We encourage features regarding upcoming events, but there are some cases in which past events will make a good feature. Good examples of reports of past events are the Women of Fearrington article informing us of the success the "Dress It Up!" accessory sale results, which can still be seen on the WoF website, and the Adopt-a-Highway pick-up reports.
Speaking of rhythm, timing is everything. The website has its busy times and its slower times. Towards the end of the newsletter cycle before the new edition comes out, for example, is a good time to get some special coverage.
Finally, a featured article should be different from your newsletter blurb -- expanded or, ideally, completely new. It could be an article written for your group subsite's Home and News page. It should be written well and look and read more like an news article than a poster announcing an upcoming meeting. Poster-like formats are strongly discouraged as they need editing and formatting to make them website-friendly.