To me it makes more sense, if he can live for 2-3 years off savings in NYC, to live there. Also, he didn't just seek a job in the "dying financial sector" (are we really naive enough to think it's dying?), but rather applied for over 600 jobs in a range of areas including supervising admissions at a college.
Applying for jobs can be soul destroying. A good friend of mine has applied for a lot of jobs in the past 6 months, but when there are only a few in your chosen field with a large number of people applying for them, and applying gets you no replies it can feel like pouring time into a black hole. It's easy to point out what somebody should be doing, but it's several orders of magnitude harder to actually do it yourself.