Note:YouTube took the free videos down because they were "too long". I am working on setting up a new version of the course, possibly on udemy.com.
This self-paced video-based course lets you learn the basics of OpenBSD system administration, including how to install the system, configure it, add software in a reliable way, make and keep it secure, run basic network services such as email, DNS, and WWW, and use OpenBSD's famous pf packet filter to control access to your computer or even build a firewall to protect an entire network.
You need to know basic Unix/Linux commands to take this course. Learning Tree's Course 396, Unix Tools and Utilities, provides good coverage of this topic. There are also several good introductory books on UNIX commands, and even some free tutorials on the web; some are listed in my list of Unix Resources.
The course consisted of the following modules, which can in theory be taken individually but for best results you should take the entire program.
Here is where the free video used to be located.
Ian Darwin has worked with Unix since 1984 and has run OpenBSD on his primary systems since the early 1990's. He is a committer to the system, contributing to many parts of the project, and maintaining several of the ports/packages of third-party software to OpenBSD. Ian has also written and taught Unix courses for the University of Toronto and Unix and Java courses for Learning Tree International; he also teaches a Python course for Learning Tree.