Seasonally - the winter! (November and December specifically!).
Soft Market - if you rented in a hot market it might be time to move and get that lower rent for a better apartment.
Stay where you are - if you don't need to move, don't. Renegotiate some nice rent with current landlord. Landlords like tenants that are quiet and pay their rent on time.
Rent vs Buy - many great calculators that can help answer this question - it is specific to New York City and the individual. (When you start to see rents rise in large volumes, it may be moving towards a good time to buy especially in an up and coming neighborhood).
Time line - if you are staying in the city for only a couple years or your future is up in the air, rent. - Mon Sep 13, 2010
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