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Anyone operating a server on any scale should want a digital certificate to encrypt data between clients and services, whether for personal, office, or public use. That’s a broad statement, but it holds true no matter how you slice it.
Aside from the disturbing image, this article is both a thorough walk through of how to setup a SSL/TSL cert and also has a source for free certificates and very cheap wildcard certs (ie. if you want to setup a posterous clone with nailed.yourmom.com and sofat.yourmom.com with a single cert) at https://www.startssl.com/?app=40
(and with the wildcard, you would even be able to add easy.yourmom.com later on without updating anything)