Two starter homes in a modest suburb may cash flow better than a higher-priced one and it is easier to offset the cost of a vacant rental with the rent that the other property is generating. 

They don't understand the math behind any type of financial formula, so they have no idea how to make adjustments to it that allow the deal to work in their favor.I think a big part of this is the generation we live in/with, that is looking for instant gratification. 

FHA 203(k) loans The FHA provides financing for not only purchasing caps but renovating distressed properties generating an income through renting out rooms or units.

There are simply better places in the country to generate a better return.

You can specify blackout dates when the property is not available for rent if you wish to use it personally during certain times of the year.Legal and Regulatory Compliance: The management firm will ensure that the property complies with local laws and regulations concerning rental properties, including obtaining any necessary permits and adhering to zoning laws.Maintenance and Repairs: Property management firms often take care of routine maintenance and emergency repairs, ensuring the property is well-maintained and ready for tenants or guests.This arrangement allows you to enjoy your second home for part of the year and generate rental income when you're not using it, with minimal effort on your part.

But I’ve been given the reins of the business and am hoping to learn and grow into something that can build a level of generational wealth that will benefit my family (siblings, cousins, and children) for years to come.But I am filled with doubt in myself and skepticism about how real the success stories really are.

. - the cost starts long before any generated income.  

Meanwhile the prop sits vacant generating zero income and costs you money.  

Maybe work in the RE business somehow; lending, assistant to an agent, the trades or start your own business like lawncare or landscaping to generate money.

Essentially he rehabs his properties to make them undeniably high quality (not just "good enough" for section 8) in order to generate a huge demand and thus be able to be extremely selective in his tenant screening process.