Linode users may be interested in this event, being held the weekend of September 25-27. 50% of the population of North America is within a day's drive of Columbus, Ohio, and basic registration is free!
This year's theme is "40 years of UNIX" - keynote speakers are Doug McIlroy, the man who invented UNIX pipes, and Shawn Powers, Associate Editor of Linux Journal. It's not just a look back; there are presentations on Drupal, Ruby on Rails, using Python for system administration, Samba, web application security, and many more subjects likely to be useful to you in running your Linode.
As noted, basic registration (aka the Enthusiast package) is free, and gets you into the Early Penguins' Track talks and pre-party on Friday as well as the main event and after party on Saturday. Springing for the $65 Supporter package also gets you the cool t-shirt and lunch on Saturday. If that isn't enough, you can opt for the $350 Professional package adding OLFU training where you can pick an LPI cram session or courses on disaster recovery, LDAP, spam filtering, and more. Any novices you bring along may be interested in the $250 Quick Start package which gets them a computer pre-installed with Ubuntu and instruction in getting started with Linux.
The schedule of events will help you sort out all your options. You can sign up for the free Enthusiast package initially and later upgrade to one of the others (deadline is noon, Friday September 18). You'll also want to book your hotel room ASAP before they sell out.
Sunday offers the Diversity in Open Source workshop and the opportunity to take the LPI or BSDA certification tests.
There's a lot going on, but you are free to pick and choose the days and subjects based on your availability and interest. As far as I am able I will answer questions on scheduling and options in this thread, or for a definitive answer you can reach the organizers.