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Try to have just one long term renter rather than multiple short term. Also, having an "agreement" with your doorman is probably the best way to avoid any issues.
What city?
Do not do it if you live in NYC, you could get into a lot of trouble.
@EY1 I did it in NYC for almost a year. Total of 75 nights at 175 a night was a decent chunk of change.
Sweet @A1. Two of my friends landed in major trouble over this, one had to vacate and the other had to pay $7500 in fine.
@ Chicago, M1