Criminal Law Questions? Ask a Criminal Lawyer.
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Is the only access that the contractor has to your neighbor's side of the roof through your roof?
Unfortunately, while the polite thing for your neighbor to have done would have been to give you the proper notice, he is not obligated to do so in this situation and it would not be considered trespassing by the contractor.
If the contractor is not insured and any damages occurred from his work, then you would have a cause of action against your neighbor.
Do you have a copy of your bylaws or the section you are referring to for me to be able to review?
What do the bylaws say?