lovehopeful

The title of my post says it all -- I am unhappy with the way things have turned out for me since college. I turned 30, and I need advice.
I graduated from a top-20 research university in 2009. I was a very good student (3.5 GPA), but my life spiraled out of control in my senior year when extenuating personal circumstances postponed my doctoral application plans. After two years of low-paying data entry temp positions, I enrolled in a master's program. First in social work (couldn't land a job after graduation) and later in education (studying the history of education fascinated me). I finally applied to doctoral programs with no success (all rejections). But  the hopeful side of me believed that I could work in a college or university with my master's in education. Both my master's degrees were from top-5 programs. Unfortunately, I got job interviews but no full-time job offers. I could land part-time/temporary work but not the coveted full-time job that could launch my career.
Disappointed with my lack of progress, I uprooted myself to the Washington, DC area hoping that would improve my employment options. I picked DC because I owned no personal vehicle and public transportation was very dependable. With no luck of landing a full-time job at a nonprofit or university in DC, I enrolled in another master's program in a related social science field. I landed several teaching assistantships which have helped me professionally but I feel academically unchallenged and unmotivated -- I can capable of doing doctoral-level work. When I applied (again) for PhD programs, I got all rejections. Meanwhile, I have continued to apply for full-time jobs with no success. Federal employment is also unrealistic due to veteran preference. 
I think "cultural fit" and lack of stable history has much to do with my dismal results. I feel over-educated for entry-level positions but under-experienced for middle-management positions. If things don't improve in a year, I may move back with my parents. As I get older, I get more depressed that I picked the wrong fields (despite doing well in them). If I do not become a university professor (which is possible), then I do not mind a director role in an education nonprofit or university administration (not student affairs). Is this career path realistic without a doctoral degree?