Thought I'd update.
So I didn't go back to school. I completed a couple of certifications (A+, N+) and finally landed a job with a regional not-for-profit. I'm making the highest salary I've ever made, and actually about 4 dollars an hour more than what the Fortune 500 company I interviewed with had offered me. Im not making a fvk-ton of money, but definitely more than what I expected to get based on the comparable starting salaries for similar jobs with no professional IT experience.
I was actually surprised that a non-profit that gets a bulk of its money from federal grants, would actually pay more than a private sector job. What's even more surprising is that this is a job in the burbs, and similar jobs down in the city are really low-balling entry level IT professionals as well. Im talking like city companies offering 15$ an hr or less, which isn't terrible in some of the small suburban towns near me, but is definitely not great for a job in NYC.
The health benefits are decent, but not great. And the time-off is about on par with what federal employees get starting out. The company even offers education reimbursement, so I'll be taking advantage of that for more certifications and maybe even a Master's one day.
Anyways, the career change took me a little time, but I finally feel like I found my calling. Thanks to everyone who gave me some good advice in the thread.
EDIT - What really got me noticed by the hiring managers was my degree combined with my certs and technical aptitude. They said the college degree made me stand out. So I hope any men who ever read this post know the value that a good education can bring.
The best combo though is education, certs, and experience. I think I made it over the experience hurdle due to my personality and technical knowledge from years of working with computers (despite it not being professional experience.)