Wow, superb post, Bert. Very thorough.

For Essentials, your own domain name isn't really necessary. Unless you already have a website, I'd stick with the free domain name and SSL certificate they give you. It's not like anyone else will be using it besides you. It will be something like https://yourname.remotewebaccess.com. Again, this is essentially for your personal use so need to go out and buy a domain name. Some people complain that it's a long name to type. Use that site in conjunction with a link shortner. https://bitly.com/ or http://tinyurl.com/ For example, https://bit.ly/tomastoria or http://tinyurl.com/tomastoria . Which are both shorter than https://remote.domainname.org. For Standard, it's kind of necessary with email, SharePoint, and RWA.

It just seems like an unnecessary cost with $50/year for the SSL Certificate and $2-15/year for a domain name for Essentials. Standard is a different story. Again, I tend to buy them 5 years at a time. That way, when it expires, I know it's time to upgrade. You also get a bulk discount.