Not to play Gloom and Doom as I am genuinely curious. 

He’s gotten amazing returns and genuinely enjoys the user-friendly features.

Go hang out in a room with genuinely wealthy folks for a while, see what they’re doing.

2.) at what point to banks recognize rental income as income?  

You need to understand your contract in and out.You need to be able to be genuine, trustworthy transparent (and this comes with experience, and /or knowledge)You need to be an authority in anything and everything Real Estate (again this comes with experience and knowledge.You need to understand your back-end buyerYou need to understand the sellerYou need to be a master at lead generationYou need to know how to deal with seller objectionsYou need to understand all exit strategies business models (flipping, wholesaling long-term, short term rentals, and everything in between)Need to understand the legalities of wholesaling.The list goes on.Does this mean that as a newbie you can't start wholesaling?

We see a regular cycle in MD where it takes about three years before investors start to recognize their losses on the properties that don't redeem, and they are unable to make up losses through prperty sales.

And pitch it with confidence and excitement but be certain behind that is genuineness.

You do not have to give them everything they want, but they should feel heard and should feel like you genuinely care. 

Your response was genuine and insightful.

If you consistently analyze properties, it will be much easier to recognize a good deal when it shows up.