I was asked what punishment I wanted. 

Suing the HOA/Management is almost like punishing yourself. 

You can easily leave with no legal punishment... you know that right?

One worry I would have is that, if it comes to evicting them, a judge might find it too punishing to increase the rents that much right away, and allow them to stay.I think I would try to approach it like:  "We bought this house with the intention of updating it to a more current state, and to do that, we need the house to be vacant (asbestos, lead paint, mold might make good reasons if they are true concerns).  

Any person who violates this paragraph commits a felony of the third degree, punishable as provided in s. 775.082 or s. 775.083, or, if a corporation, as provided in s. 775.083

Speaking of this have you come across the punishment for paying interest?

You never know ,so offer something  Boy, I don't think I could stand punishing myself this way.

If the property was indicated on the lease as vacant, and he has no signed proof of any other agreement about personal items being left behind, those things he listed are not your problem, and not "punishable" unless identified in the lease agreement.  

Although property taxes are not as punitive as TX, state income tax is among the MOST punishing.  

Do things with clarity and good purpose for all to see, and it is amazing how word spreads like wildfire and entire communities get out of your way or step in to give you a hand.If you try to come here to "stack and stack," make your pile and get out in three or four years, Pittsburgh will punish you.