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Don't know what you are trying to say by stating 'grandfathered 2 flat'. Any 'grandfathering' needs to be verifiable to July 1957 for the building code. Forget the Zoning dates. You can rent out anything you want, it is done all the time. If the City comes in, Zoning is often times not even on the complaint. Corp Counsel may amend the complaint and add it on at some point but not usually. Typically, there are enough building code violations not to make it necessary. Occupancy is occupancy. The DOB isn't going to worry about whether it is a home office or someone is sleeping there. Granted if you hire an attorney or you make that distinction, the City will squash that position. Egress, ceiling height, natural light and ventilation are the bigger issues that would come up. There are also other conditions that would need to be met for legal occupancy.
Zoning issues tend to be dealt with more if you are trying to run a daycare out of a house or mechanic shop out of a garage, etc.
In short, you can do what you want. It is highly unlikely the City will come knocking unless your neighbors make a phone call. If you do rent out the space, at least make sure that it is safe and not a hazard.... more