Not to get too personal, but based from what I read on this site you are just a few short steps from landing a Broadway gig. And you don't have to answer this, but when you do get it, will you be satisfied? Will there be no more steps? If so, how will you handle that?
(and again I apologize if I'm getting too personal)
A few short steps away from a Broadway show . . . well, those can be big short steps.
What will satisfy me . . . I think it's becoming less and less about a destination and more and more about the journey.
For me, the reasons to work more in commercial theatre are all about means to and ends. One, to be able to work and stay in one location to spend more time with my partner. Two, make more money when I am working, so I can take stretches of time off. Three, make more money when I am working, so I can pick and choose and the projects I work on. So, I am not seeing Broadway or Commercial theatre as the end, but as a step in my career growth. I am also looking down the line to teach, and the more variety of experiences I can get on my resume, the better. I also know the type of shows I enjoy working on lend themselves to being produced in a commercial theatrical setting.
I know that Broadway or other commercial theatre will not be the answer to all my career goals - and I know myself well enough now to know that there is really not one thing that will satisfy me. (Other then a regional theatre type job in a big city that does a variety of work, allows me to both PSM and ASM, pays me Production Contract money, and allows me to rehearse a show every three months, and take off time when I want - oh, and a teaching component . . .)
And it's just a fact of life, that there is often a termination point in this career when you are just done with the career or the career is done with you. What next? Who knows. I don't think you can plan that far in advance. One of the reasons I went to grad school was to open up teaching as a possibility. I am intrigued now by producing, company management and other elements of that world. I would also be interested in Production Management. Outside of theatre, I feel like I can bring a lot of my skills to other areas.
But, you do hit on something I feel very strongly about the fact this career can feel a lot like a drug addicition - where you are looking not only for you next "hit" (job), but also find that you need to find a bigger and bigger "hit" to give you the same buzz. Which is good, because you often need to find the intangible things - like the buzz you get from the job - to make up for what you don't make in pay, status, or hours.