Quote from @Dawn Harris: We have a STR managed by a property management company.

It isn't having paid off properties that offers security, there are still taxes, insurance, maintenance and management involved. 

Many investors in NY like the idea of house hacking because:- They can invest with a low down payment (similar to what a 20% down payment would be OOS)- They gain hands-on acquisition, project management, and property management experience.

Alternatively, keeping the properties offers long-term equity growth but with lower cash flow.Ultimately, weigh your ability to manage future cash flow, your risk tolerance, and your long-term goals.

You're picking a great time to start investing, the area is becoming a hot spot for investors. 

Wherever you go, you are competing with local investors who feel the same way, except you have an additional cost burden and management inefficiencies because you are NOT local.

Airbnb can be tricky, there will inevitably be bad guests or issues with the rental – but adding value on the front end and managing the guest stay appropriately makes all the difference.Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Try interviewing at least three managers.1.

Capital ExpendituresNo Property management because I manage my own.

You also have to have at least one dedicated parking space and the manager has to be available 24/7 to be on-site within 30 minutes.