Allow me to play devils advocate on a few things...
1. Why does Barry hire these people who have drug habits or are felons? I work in the emergency department and have my fair share of patients that come in for work injuries or patients that come in for other reasons. When I'm obtaining information, I've noticed that a decent percentage of patients who work in construction or in those trades mention drug use in their social history or have drug abuse in their medical history. It definitely goes hand in hand -- please dont think I'm saying that every person who works construction is a drug addicted felon.. but definitely a decent percentage.
I assume a company or contractor is less likely to do drug testing or background checks and these people may be willing to work hard for the opportunity presented to them.
2. Why is her family broken because of this? I don't know the specifics of her family dynamics, ie.. married, children, ect. I'm wondering if her significant other didn't also already suspect an affair and this basically sealed the deal for him.
All of the above are just thoughts bouncing around in my brain.