oy, I love/hate this thread. I'm one of those OOT people that got stuck in NY (although I'm not sure if my neighborhood is considered NY by real NYers).
As a little background, I always said that NY is a great place to visit but terrible to live. As a matter of fact, one of the first things I told my parents when they asked me what I'm looking for in a girl when I started dating was that I DON'T want a girl from NY (actually I may have said Brooklyn). Well, as they say, G-d has a sense of humor. Not only did I marry a girl from Brooklyn, I now live in 5towns/FR. (Obviously, there is a hashgacha pratis story how I met my wife, agreed to go out with her, etc but that's for a different time.)
So, after living in EY for a few years after getting married and living in Elizabeth for a year afterwards (wife had to do a year internship in the tristate area to finish her Masters, and I refused to move to Lakewood, Brooklyn, Monsey, etc.) I was ready to move OOT. I didn't have any for sure jobs lined up but a few possibility starter jobs. Then I get a call from relative of mine who had an opening in his company. It was a well paying job (way more than any of the possibilities that I had at the time OOT), with huge potential for quick growth. Problem is that it is located in Queens. I spoke to several people/rabonim and I took the job and moved to FR. Two years later, I bought a house in the five town. Anybody hear of Inwood? 3 years ago, most people didn't. Its the 'lost' 5th town. There were about 15-20 families here at the time. House was small but affordable (and I have property. I'm now in the process of getting permits to double the size of my house). Community now has close to 60 families.
So now, I'm in an OOT type community (friendly people, only one shul/Rov here, affordable housing, kids have a nice size back yard to play in, neighbors mind their own business, etc.) but with all of the in-town amenities near by in FR and 5towns (a 5 minute drive max). We have all of the stores that we need, restaurants, schools, minyan factories,etc. And I have a very solid, stable, well paying job. Yes, it takes me 45 minutes usually (but sometimes up to 1:15hr) each way to/from work when it is only 14 miles away but that could easily change since there are plenty of job opportunities in my field nearby and it's just a matter of me deciding to move on from the family business.
In short, I would still love to move OOT but I think I'm stuck here because of my job. My position in an OOT community pays much much less and at this time my family is not ready to make the move (kids are a little older, my wife has a good and well paying job, we own a house, etc). But there are several communities in the greater NY area that offer many pros of both, an OOT an intown community.