Instead of jumping into an expensive Long Island market with negative cash flow, consider investing in a Texas market like San Antonio, Houston, or DFW suburbs—these areas offer strong rental demand, lower property taxes than NY, and better cash flow potential.

It will depend alot on the number of beds offered and the size of the home overall; do you have enough indoor and outdoor seating for 9 guests?  

Jackson, Madison, and Ridgeland offer great opportunities for successful investments.

Ask the right questions, pause, and truly hear what your sellers are telling you before offering solutions.Bring the Value: Educate.

Most - 90% of VRBO requests, do not get the discount, but to be fair, we offer the discount on both platforms.Believe it or not, we get requests from Airbnb users with upwards of 40+ 5-star reviews. 

Taxes have to be paid, so does insurance, what about maintenance? 

You don't have to spend money  out of the pocket on searching Redfin, making some phone calls, making offers and posting ads on Craiglist or whatever local media you want to use to sell the property.

A few others have called out Hemlane, who appear also quite responsive here on BP and also offer a degree of repair/work order management baked right into their middle/upper tier offerings (versus having to bolt-on as with RentRedi + Latchel). 

My biggest conundrum now is I want to be my own GC because even when I play with smaller numbers they’re still out of reach for me to be able to attain this goal and afford the monthly mortgage with taxes and insurance.

While a properly maintained TN LLC might be sufficient for those who diligently follow corporate formalities, the additional layer provided by the Wyoming entity can offer significant extra protection, albeit with increased complexity and cost.