Career Advice...English Teacher back to IT

offthenonagainoffthenonagain Member Posts: 8 ■□□□□□□□□□
Hey guys, I'm needing a little advice. Some background: I've been teaching English in Japan for the last 4 years. I've really enjoyed it, but I've realized that this is not what I want to be doing for the rest of my life. Before I moved abroad I ran a freelance IT company for about 5 years (did some web design/hosting, SOHO network setups, custom PC builds) after high school and during college, was a web developer for a fraternity, and worked the Help Desk at a University for about 2 years. As far as education, I've got a BA in English Lit and a MBA with a concentration in Information Security Management. I'm wanting to move back to the US and get into a network/sys admin job.

My questions:
What's the best way to handle the ~4 year gap between my last IT job and now?
Do people list freelance work on their resume? I never incorporated or anything, but I had a few dozen clients over the 5 years.
My experience is varies pretty wildly (Web Development, Help Desk, Consulting) should I list it all, or just help desk job?
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