Quote from @Carson Hyland: Even if you buy the right property, failing to manage it well will kill your cash flow. 

If you are unsure, to start, hire a property manager and don't let the tenants know you are the owner. 

Just want to drop the message here, anyone located in Dubai or distanced managing properties there?

Capacity and Tolerance. 1) Capacity: how many people can you comfortably fit in the property, is there room to add more, or add more value to the tenants to increase rent.2) Tolerance: How many people are you comfortable living with, if there are vacancies are you able to handle that.House hacking is an amazing path to homeownership, and a nice low barrier to entry into self managing your properties.

For example it is my understanding that Big Bear allows it but whoever is managing the property has to live within 1 hour of the property. 

If there is a property manager, your success rate is going to be very low.   

Not a rookie - While I have never purchased a home without an agent, I have purchased two homes in the last fifteen years in Denver and, at some point, managed both with some form of rental income, plus helping my mom manage the independent basement apartment in her home.

. - Your portfolio will suffer:(You want a PMC that has great systems in place, including a great portal where you can keep tabs on eveything.You will also need to manage your PMC on a regular basis.

Looking for feedback on an approach to help grow my hospitality portfolio.   

The local property will give you practical management experience.You might do better buying a REIT if you are planning to buy single properties far from home.