Replace your unproductive habits with productive ones.

My lease says that the home was bug free when they moved in and if the pest control company determines that there is a new infestation caused by their dirty living habits, then they are responsible for the cost of the treatments to remove the problem.This hopefully motivates the tenant to be more careful with things like leaving food out for days.

I state in the lease that damage from smoking can cost thousands of dollars (replacement of flooring, curtains, blinds, re-painting etc.) and that they are on the hook for paying for it if they lie about their habits and smoke inside.

Check Mint to see how much you’ve spent on dining out this month and the implications those burritos might have on your bank account.There are countless apps for managing your money, some like Money Desktop offer free investment advice; some are geared towards small business owners while others are FDIC insured “piggy banks” that also track your spending habits.

What's left ( if any ) you should put into savings.It won't be easy due to the bad habits you may have developed money wise over the years, so don't get discourage when you relapse and spend it all at the bar one night.

Most people who smoke cigarettes indoors habitually aren't alone in their habit.

If they were running out of cash they could have cut corners on vital areas. 

Habitability indicates that potable drinking water must be present and available. 

- I am not a lawyer so take this as it may, but reductions in rent typically are for "habitability" issues in a unit or promises / guarantees.

It would be far easier if he handled the rentals, but his job provides vital income and he loves it.