Here is my plan. Tell me if I'm in over my head.

[Keith Aiello]

I am currently working as a nurse working 12.5 hours 3x a week. I aim to get out of this career as I'm not happy in it and I plan for a transition to real estate. Not only for some financial freedom eventually but just to work for myself.. 

I am looking to get my real estate license and try my hand at sales but mainly because I hope to purchase a home in the east end of Long Island. Area of the Hamptons primarily. I hope to buy a property for short term rental during the summer. With my license I can save on closing costs and commission. From my own research and airdna, the area is in high demand, 97% of rentals are booked in the high season months for 30 days. The range of price is $250 -$500/night per bed - I currently have a 30 year mortgage on a $600k home with 5 years equity of around $180k. My fiancé is a doctor and shares this home and mortgage with me. Some of these homes in the Hamptons ask for between 1-2 million. Am I way in over my head to say that I would like to take my savings ~$50k and home equity and use this as a down payment for a Hamptons home, list it to airbnb and vrbo and allow the income from that to pay for the mortgage for the home until its paid off, becomes profit, and then I can back away from my job as a nurse and focus solely on real estate investment and short term rentals?

Looking for some people who can steer me in the right direction. Thanks!