I feel like I'm doing something wrong though because it seems way too easy.

There is nothing wrong with a condo as long as you are aware of the downside with the hoa fees and hoa rules (potential for them to convert to owner occupied only). 

They want to ensure that if something goes wrong early in the deal that you have enough to cover expenses.

I’m sick of being hosed by these guys and I expect every contractor to be wrong with their estimate.

Even when people made mistakes buying the wrong property hired the wrong people, analyze the deal incorrectly got saved because of the strength of the market. 

Am I looking at something the wrong way?  

@Andrew Taylor there is nothing wrong with your idea, but you have to get buy-in from your city council.

What is wrong with this thing.

This could go wrong so many ways.

Given this is not a cash loan, and I would be using a home equity line of credit from his paid off primary residence, correct me if I'm wrong, he should expect to pay ~4% interest once the line of credit is used.