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Ask Curbed: Sublet Etiquette

[Yesterday, we kicked off Ask Curbed, a new feature in which you, uh, ask us things. Ready for another go round? Of course you are. Let's rock.]

A Curbed reader sends along a question about subletting, a confusing micro-world that never gets old. Her query:

I was hoping you'd be able to enlighten me about subletting my apartment…I'm about to renew a 2-year lease for my rent-stabilized studio in the Village. "Real" rent is $1440, currently I pay $1250 and with the renewal, there will be a 5% increase. I'm going back to school for a year and will probably need to sublet it. People have mentioned that I should charge the subletter more and make some money off the whole arrangement. What are the legalities associated with this? Do I have to let the property management company know about my sublet?
Your thoughts on the fine line between life and law in the comments, please. If you've got any good subletting tales, this would also be the place to air 'em out.