Please, folks don't judge others by your particular state statutes (if you even know
yours by heart, which I doubt).
Self-help in Florida is done every day. I have done it several times, mostly pan faces.
I have scraped lettering off a window a time or two as well.
The OP's boss really has some brass if the posting is true and not a joke.. It is one thing
to repossess a sign face that hasn't been paid for...but to leave that replacement
is a bit over the top, IMHO.
As to all that noise about trespass, etc...if the boom truck is parked on public property
or adjoining private property and can reach the sign, it is fair game. If the
police enforce trafic rules on a property, such as running a stop sign in a mall parking
lot then that property is quasi-public property and being on it to repo a sign
shouldn't be a trespass.
If you extend credit, which you do by allowing the sign to be paid for later, then
the state's credit laws apply. Hopefully there is a good writing that is unambiguous.
If you don't show up for court, your bondsman can send in a bounty hunter and
s/he can smash through your doors to get you and take you into custody.
If you don't pay for your motor vehicle, the lien holder will have a repo guy take
the truck, car, boat or plane right from your driveway or yard. All that and more
is perfectly legal. Know the law and your rights before extending credit.