While on Twitter one day, I saw the cries of one Sarah Maliphant, a professional Coach and Mountain Leader. She had an existing site on wordpress.com, but was looking to take her site to the next level by moving to a self-hosted WordPress site.
After getting in touch with her, I helped her by answering all of her questions and concerns about what moving to a self-hosted site would mean, as far keeping her custom domain name, her images, content, and the appearance of her site.
Once we discussed all the details and developed a plan for transitioning her site, I set about making the transfer to her new server. The transition went very smoothly and the site was just as she had left it on wordpress.com, except now with the ability to install plugins and modify her theme.