The 3 month move in cost upfront kind of feels like a punishment if the market as a whole charges 2 months.

Wholesaling in many states - including mine - is considered the unlicensed practice of real estate and it comes with a whole lot of bad: "Unlicensed practice of real estate is a third-degree felony punishable in criminal court, for each violation, by up to five years in prison and $5,000 in fines."

Are you effectively punishing them because they are moving out of their home for the first time?

The complicated answer is make sure you have all of your ducks in a row or face punishment.

They no longer let you turn down guests easily or you get punished by airbnb by going low in the ranking.

When the basement tenant sends a text to keep it down or tried to set an agreement not to do laundry after 10 pm, the upstairs guy will almost "punish" him by not giving him his mail or do laundry even later or tie up the washer and dryer all weekend and still play his music loud, or be loud in general.

The investors will punish them. 

Emotional support animal protection is meant to protect a person with an emotional or mental disability, the law is not made to punish the landlord.

You are a glutton for punishment are you.

Meaning if you kill someone by accident your punishment is less severe than if you do it on purpose but that is not the case with securities law.