negotiating rent following a sublet

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I think you need to see what comparable apartments in the area are going for and go from there. I have to imagine a landlord who got $9300 in 2008 doesn't want to hear offers anywhere near $5600, but maybe the prior tenant grossly overpaid 2 years ago. Are you trying to justify the current rent? This all assumes you dealt with the prior tenant on the $5600 amount and not the landlord of course. Good luck

You have to do a bit of homework and have a list of comps with you.
You must also have to show a willingness to move, no matter how far or near to the truth.
If your landlord knows you don't want to move, comps at $2000 a month won't even help you.

First thing to establish is where the market for your place is, which you would know better than anyone else. I imagine that $5600 was discounted because it's a sublet that goes into this situation you are now facing.

However, what was the next best-priced option you had last year for a comparable thing? Do you have a sense of what the sales price of the apartment would be? These things will help establish the "right" rent for the place, and figuring that out is required before strategizing.

INteresting. I think the landlord has a strong hand here because you've already fallen in love with the place, and even if the "correct" price is too high, if it has all of the strong features you suggest, the landlord might be ok letting you leave in exchange for another tenant to pay more even if not quite to the level of the prior 2008 price.