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!

[Taylor Dasch]

It does sound pretty risky and definitely let your own research hold more weight than AirDNA I have found those numbers to be slightly inflated in my market.  The home needs to cashflow from the beginning, if your purchasing an expensive home it should produce results for you. If I understand correctly your planning on having the AirBNB pay the mortgage until the mortgage is paid off then you can retire? That will be 30 years anyways and you could have hge growth in 30 years if you just buy deals that cash flow and let it snowball into massive wealth. You can literally buy a 12-18 unit apartment complex for 1 million in my market that cash flows from day 1