How realistic is my plan to rent a 2 bedroom apartment in New York City specifically with the intention to Airbnb the second room in hopes to cover the entire cost of the apartment?

You shouldn't be trying to get tourists to pay your part of the rent, period. Also, if you are charging 200-250 per night for a shared apartment, it will be hard to compete with hotels in that area which are charging the same rate for much better service. I rented a room in an apartment that I lived in for about a year, and figured how much to charge based on the extra room being occupied 3 nights a week. I divided what I would be paying on the vacant room (half the rent of the apartment) by 12 nights a month, and added a bit extra for the things I bought to furnish the room, towels, food, etc. I had an occupancy rate that was usually higher than 3 nights a week, and treated that as earnings. You also have to see it as a part-time job; responding to inquiries, cleaning between guests, and waiting for people to arrive. With that in mind, do you really expect to earn $2,250/mo. doing menial tasks like cleaning and replying to emails? That's about 90 hours at $25/hr. It's really not fair to expect someone to pay for their stay and yours just because you hold a lease. And you'll have better luck if you charge a fair rate based on a lower occupancy rate. Another thing to keep in mind; AirBnB does not pay taxes, but they submit a form to the IRS reporting the income you make from your apartment, so you need to calculate how much you will pay in taxes and set it aside. I have a feeling this will come under greater scrutiny in the near future.

You're going to have to make sure this is not going to irritate the neighbors and building staff. $200-250 per night is really high. You should expect more like $100-150. Even if you find out you're able to charge higher later, be conservative in your projection. Furthermore, tourists generally prefer to be in Midtown, so your location is not ideal. PS: In response to Shelby's answer, it's not illegal if the host lives there with the guest.

AirBnB is much much harder in a doorman building with full service staff than in a building with only a live in super.  Why?  Because landlords don't like AirBnB and the more staff you have the more people will be reporting you to your landlord.  Eviction is forthcoming. If you'd like to live in an apartment you can't afford and make up the rent with AirBnB or other short term subletters that's a definite possibility.  If you want to live in an apartment and never pay rent by renting out your spare bedroom that's more difficult.  Your goal was to make 4K+ from AirBnB to cover most/all of the 4,500 rent.  You're just not going to get 200-250/night for a shared apartment likely with a shared bathroom.  Unless you're including something that the people can't get elsewhere (i.e. sex, drugs, a live in personal chef, etc).  Assuming you can't afford to offer any amenities besides the shared building stuff that hotels offer for less, you're looking at 75-150/night.  Especially in the FiDi - not a super desirable area to live in unless your place in on a high floor, overlooking the water or 9/11 memorial. Your best bet for covering a good chunk of your rent is to live in a mid-tier building (elevator, laundry in unit, secure access, maybe a small gym, NO doorman, no service staff besides the live in super) in a more desirable area (near Times Square for tourists, East Village/Greenwich Village/UES/UWS for less horrible tourists or people coming to visit friends).  You should have an apartment with 2 bathrooms and be renting out the master suite.  If you can find a duplex or apartment with 2 entrances all the better.  You should not have any pets or other things which will limit your customer base.  You should consider just getting a part time roommate (think flight attendants who are gone half the month or more, people who travel 75%+ for work).  Your other option is to live in a super cheap apartment and have rock bottom prices on AirBnB - you'll have your room filled most of the month, but at that point why not just get a roommate?

Have you ever leased an apartment in New York? The landlord will likely deny your lease application, unless you could prove that you have an annual income of about $180k (for a 4500/mo apartment). Alternately, if you don't have a pre-determined salary, you could prove that you have more than a year's worth of income in cash, or have a guarantor worth more than 180k per year sign the lease with you. Additionally, the financial district is not an ideal neighborhood, especially for tourists. There is little in the way for New York's fine dining, sites (save for the WTC memorial), or the city's cultural attractions. There's a reason those cheesy high-rise luxury buildings have to offer so many amenities to lure residents.

200-250 per night is not realistic for a bedroom in a shard apartment. People who get that type of rate are renting out an entire unit. Look carefully at your Air bnb comparisons. No one will pay that money for what is essentially a roommate situation. And a 75% occupancy rate is really uncertain -  I think overall Air bnb is less well suited to high end properties.