The OS X Terminal is commonly used for establishing remote connections, and has some options for facilitating this.

Remote Desktop lets users control their desktop computer remotely. It’s a simple concept that, properly implemented, can have a dramatic impact on your organization’s productivity so that staff can ...

Server 2008 R2, on the other hand, is a much different story. It has a revised kernel, it has a new user interface, and it isn't a drop-in upgrade for that entry-level server you bought six years ago.