SenorBeef,
At this point, it looks like you need a plan. You can’t move toward a goal if you don’t know what the goal is. Sounds simple, but a lot of people forget this step and get overwhelmed by all those choices on Dice, Monster, and specialty websites. It sounds like you’ve seen this already. It’s a two step process. First, decide what you want to do, then market yourself to those jobs.
Well, what do you want to do? Don’t let your past constrain your view of the future. We’ll get to that in the next step. This is the wish list, what you like to do. Do you want to do run the network? Hardware installation or software integration? Training? End user support? International or national travel? Any specific industries you like, such as banking, gambling, defense, medical? Narrow this down to 2 or 3 distinct job classifications. Skimming Dice or Monster can give you ideas of the wide variety of options available.
So now that you know where you’ll end up, how do you get there? Successfully market your self to those jobs. How? A great cover letter that generates enough interest in SenorBeef that the hiring authority wants to talk to you. Short and sweet, an introductory paragraph that identifies the position you’re applying for (referring to the source, too), 2 or 3 paragraphs that match your qualities to those specified in the job description, and a closing paragraph that includes your e-mail addy, phone number and, most important, asks for an interview.
I emphasize the cover letter because the hiring authority usually sees it first. If he likes it, he’ll either skim your resume and/or put your cover letter/resume in the callback pile. This is where you can make his job easier by pointing out explicitly why you’re the best person for the job. While you’re at it, include something that makes you stand out from the crowd, something that the recruiter who’s looking through a few hundred cover letters is going to remember. Could professional poker playing generate some interest?
Let’s take a couple of points in your OP. A 4-year resume gap, you say? I see an opportunity to show how, as a professional poker player, you take initiative. You take risks. You can read people. You’ll probably be great dealing with users or customers. Systems education with no specific experience? I see someone who doesn’t have a bunch of bad habits the next employer will have to break. Someone with a bedrock upon which the new employer can build.
I apologize for the incoherence. It’s getting late here. Plus I like giving job search advice. I love the thrill of the hunt when I’m looking for a job.