Corey - unfortunately the job market sucks out there, retail or not. My husband has been looking since December/January and he has a business degree. We're in Ohio, close to the Indiana border, so it's a similar economy. He's had 9-10 calls the entire time he's been looking and he's applied via craigslist, monster, classifieds, and even networking contacts. He has a similar problem of changing jobs and then spaces in employment, but for different reasons than you - he was a student for several years so he had to sometimes look when his schedule changed, then we moved here from TX to OH for my job, then he was in an accident and had back surgery, and he was laid off last year seasonally (but the business didn't recover enough after the season to invite him back). We are fortunate enough during this time not to have kids to add to the financial stress, but I think I've been very patient with him not getting a job. Never have I threatened to leave him if he didn't get a job, even though I get frustrated when he refuses to look at temp agencies. In fact more times than not, I am standing up and trying to boost his ego, since the long job search alone can strip someone of what confidence they may have.
As for going to school, don't be afraid of college math - there's little above the algebraic level unless you major in mathematics, finance, engineering, economics or physics. You'll also find that education is much better as an adult than it was when we were younger - I got so much more out of graduate school than I did in undergraduate and my mom had a better time getting her college degree when she got her degree nearly at the same time as me, than her attempt when she was younger (when she almost failed and then actually dropped out). I have been trying to convince my DH that this might be the right time to get his graduate degree (he wants to be an employment rights lawyer), but we are going to hold off until I get a more secure job, preferably better paying, since I've been told I am being laid off in June.
You are not alone, Corey, and hopefully the advice presented by others will help you. I just wish your DH was being more supportive during this rough time.