You will have to have a set of very clear rules, consequences for breaking them, and a way to maintain oversight.

Consequently, he ordered all the materials for both homes at once.The guy that is using Home Depot has spent a few hours having Lowe’s and Home Depot price match each other.Again, I don’t have a dog in this fight, and I don’t understand the accounts either of these places have for contractors. 

This sounds like a situation that is possible but could have severe consequences on my behalf.

Your lease should say when her rent it due, i.e. she doesn't get to choose the date she pays you (at least not w/out consequence). 

My nature is complete honesty no matter the consequences.

People who avoid confrontation when simple honesty can save loads of time/money slows every industry - and consequently - the world down.

My questions:1: What is the consequence if the seller agent doesn't disclose his interest in the property?

As a consequence, those landlords who cater to social housing clientele tend to perpetuate the stereotype of slumlord.There are other programs, such as group homes for physically or intellectually challenged youth, which will pay much closer to market rents, but do involve a little more red-tape than your regular lease.

My guess is an unintended consequence from policies like $15/hr minimum wage.

It's not worth saving, and then be liable with very costly consequences.