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Hi, I am Leon, a NSW Solicitor. I will be assisting you with your question. If you choose a telephone call, you will be charged an additional fee.
You will need the character references to assist in the amount of jail time he will get and also if he is suffering from any medical condition that should also be provided to the court.
Habitual offence declaration is when the RTA issues him with a further 5 years disqualification if he has has 3 from the court in the last 5 years.
Here is some further information. http://www.sydneycriminallawyers.com.au/blog/what-happens-if-you-are-declared-a-nsw-habitual-traffic-offender/
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