what are the chances of me winning a civil suit if I have a written agreement signed by both parties? How many times prior to filling do I have to try to contact that person to collect debt and what if that person blocked me for contacting them?
That is not nearly enough information to answer your question. The contract, and the surrounding details, should be reviewed by an attorney with some experience in the filed covered by the agreement. If this is a non-compete you need an employment lawyer; if this is a lease you need a real estate lawyer; and so on.
Answers to questions are for general purposes only and do not establish an attorney-client relationship
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