<prompt> Human: Tl;dr: Should I pay my yearly rent upfront in cash for a ten percent discount? specifics:I live in NYC where housing is a major pain. I pay 3600 per month. I have roughly twice the cost of my yearly rent in cash right now and a salary in the normal range for that rent. The cash sum is not part of my emergency safety net. I have been at my job one year, things seem fineI would not pay upfront without at least a ten percent discount. Will likely ask for more. If my life goes as planned ie I dont lose my job, I intend to stay in this apartment for the next 2-5 years. I will definitely be renewing the lease for another year regardless of how I pay. Ive lived in this apartment one year already. My building does not allow leases of less than one year. Does it make sense to pay my rent upfront if it means Ill save more than one months rent? Since I plan to stay in the apartment, and thus will need to sign a one year lease and pay rent anyway, it seems like a good deal. My only hesitation is that some catastrophe happens and I will need to break the lease the only circumstance under which this would be the case is if I lose my job, which seems stable at the moment but Ive heard lives throw curveballs sometimes. I have also considered asking to pay in two chunks six months apart to reduce my risk slightly. What would you recommend given my situation? And thanks rpersonalfinance! Ive learned so much from you guys already and just think youre awesome!  <response>: I probably wouldnt consider it unless you could setup some sort of escrow situation for it. Or if you somehow have access to incredible, low cost legal services and the greatest documentation ever. 