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The courts are extremely busy. While it's possible to reschedule a date, you're not exactly going to get a date of your choosing.2) Is it possible to request the actual trial date scheduled for a specific date (i.e. October)?
The charge is driving while suspended. There isn't going to be much in terms of disclosure. Either your license was valid or it wasn't. That being said, you'd still probably want to ask for anything available to you.3) What documents should I request from the court (i.e. disclosure, etc.)?
Dropped based on what? You plead guilty to a charge that came with a 30 day license suspension. There is an expectation that you wont be able to drive. Your strategy was to continue driving until someone told you otherwise. The letter at this point isn't so much a formality as it is a courtesy. There are instances where some people may not realize they are driving suspended. I can't say that this is one of them. I don't know if there is much they can do for you.4) What are my chances to get this case dropped?
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