You seem a little unfamiliar with the way things really work . He obviously has a sense of entitlement , or he would not be so brazen . How does the tresspassing law read where you live . A front yard even gated in most places would not qualify for a criminal charge <unless posted>. The value of the cigar would not be enough for a cop to mess with the paperwork . Any LEO's out there ? They would know better then I would . What charges and what penaltys ?
This may have been answered. In most states trespassing is an infraction, similar to a traffic citation. Fines and no jail time. However, what he is doing can be considered burglary in some states, depending on how the definition reads in Florida's Revised Statutes (I only know Missouri and Louisiana). I would take whatever evidence you have to your local police department.
Pranks to get even are hilarious, most cops even agree, but....
You risk too much. You may or may not be liable for criminal charges depending on how far you go, but you are always open to civil liability. People can and will sue everyone for everything.
If he starts up again you may be able to work with you local LEO's to catch him in the act. But I would definitely take what you have to your PD and let them handle it because it could become a larger problem. This is not legal advise, since I'm not a lawyer, just a suggestion to let the PD handle it.
