As the webmaster for a small club, I experimented with bulk emailing and found it totally unsatisfactory. Aside from all the technical challenges from various ISP's, I found managing the multiple small lists time-consuming. Not to mention being black-listed as a spammer. So, after a little research, I selected an email service called Campaigner (www.campaigner.com). It has all the list management tools, plus an opt-in subscription process that avoids the spammer stigma. It's $25 a month and it works like a champ.