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To resign or not in the Bay Area?

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I am in the bay area working with a pretty reputable startup and have over 15 years of experience being a java developer. My last review with my manager didn't go very well. I am pretty sure that I should be able to clear 90% of the job interviews in the bay area that I won't have any problems finding a new job. However I don't want to search for a new job while continuing working in my current position and also moving to a new position in the same company is out of the question. I had a few questions:
1. Given the current job market in Bay Area how much of an issue would it be I have resigned from my current position. So for eg. if I can clear 90% of the job interviews based on technical skills, how much will this percentage roughly fall down to.
2. What will be financial costs during the period I am job hunting. Obviously I won't get paid but how much will health insurance etc. roughly cost given I am a single guy.
3. If any of you have been in the same situation, I would like to hear about your interview and other experiences, especially how to answer the question as to why you left. I will prefer to tell them that I left because of very poor work/life balance which is is a fact in my current job.
I understand the answers will vary based on the area and the job market and that's why I will like to know from developers in the Bay Area with an understanding of the current job market.

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You might want to keep the job until you have something else.  Since the last election, despite all of the ads you may see, I think most companies are afraid to hire.  My daughter has been looking in the bay area since before the election and had several companies interested until the election but since things have dried up.  

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