Don't be hard on yourself! Life is tough, and it takes several years for things to come together.
If I judge myself, a middle-aged person, by your criteria, I am mostly in the "non-accomplished" side. I have a good education and have taken addition courses. I have a low-paying job that would not even begin to cover my expenses if I were not married to a man with a better income. When I look for better jobs, employers consider me, but do not hire me. If I were younger, I would try harder, but since I am older, I have not put a lot of effort into my job search.
I had hoped to be married, and I got married in my twenties; being married has been a lot of work, but it has been worth it because it allows the two of us to accomplish more than we would have alone. However, it took about 10 years for us to figure out how to manage our partnership. Together, we can afford a comfortable, middle-class lifestyle with occasional trips or other perks. Alone, I would be poor.
When I was younger, I had wanted to be a successful artist or working writer, and neither of those dreams came about. All my jobs have been low-level and not creative. I also wanted to be a mother of two, which did happen (and kind of kept the other things from happening).
I do not feel like a failure at all, and I don't judge my value by how much money I make or where I live. I judge myself according to ethics and morals. Still, I think that you should try to maximize how much money you make just because you should be able to live alone if you need or want to. But, if you are choosing NYC as your base, you will find that prices are high, and it's going to be difficult for you to get a high-paying job when you are just starting out. If you moved to a city with lower costs, you might end up doing better.
Have someone take a look at your resume, cover letter template, and references. Make sure that you are putting in the proper buzz-words for your field. Make sure that you are putting yourself in the best light possible, without lying about what you have done on the job. This is the very best time to put out your resume, while the economy is good; if we go into recession, you won't be as appealing to prospective employers as you are right now, when some employers are finding hard to find candidates.
Good luck, be patient, and keep being positive.