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Whether the landlord is in cash negative position has no bearing on the subject of you wanting to haggle for the rent. Why not just pay what he/she is asking if you think it is worth it? It you don't think it is worth it, move on to the next place. I don't understand your issue with it if it...

Actually, I am not a lowballing type person. We have paid over the asking price on one place we really wanted badly, or generally offered slightly less than asking. If I want a place, the last thing I would risk is offending the vendor so that they refuse to deal with me. Believe me, it happens...

I also would wonder why someone who can prove to me that they have made their mortgage payments at twice the rental amount, needs to haggle to knock of another $20 per week from MY income. Especially knowing they probably have a lovely bundle of cash from sale proceeds sitting somewhere earning...