100% nightmare tenant that will likely get surprise roommates and a zoo of unauthorized pets while they live there and then claim "oh I didn't know that was against the rules".

As you know, being an attorney yourself, it can be a Sisyphean task to making a consistent 'good' living.

Also, often times the original homeowners still live in the property so once the sale is ratified you have to go through the eviction process or offer cash for keys to get them to leave.

Are you saying you want to STR rooms in the unit you are living in?

It's vital to know which state you live, where all your properties are located, your homestead (if you have one), values and type of REI business you have now and what you want to have in 3-5-10 yrs to have the right set up for you. 

@Michael Smythe the repairs were never completed while the tenant was living there.

I lived in it for a year and loved the location.

I live in a community where half the people never lock their doors.

I'm assuming that this situation wouldn't pass inspection, but one could argue that all the spaces the guests have access to (i.e. bedroom, bathroom) are safe and habitable + the guests wouldn't be exposed to the kitchen.Also, do the city inspectors inspect other parts of the home the guests won't access (i.e. inspectors check the basement for water infiltration even though no guests would ever be living or even going down there). 

If you're a single mom with student loans, a car payment, and living paycheck-to-paycheck, then $20,000 would be devastating and a reserve is critical.