Here in NH, you cannot plead guilty to a DWI and not lose your license. If you decided to plead guilty, you would lose your license from 90 days to 6 months. Also, if you are convicted of DWI, you will have to take the Impaired Driver's Intervention Course (and will likely need after-care due to the breath result). You will also be required to obtain an SR-22 (a rider on your insurance) that will cost you greatly. Please feel free to contact me if you wish to discuss this further. keefe@...
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Due to the amount of merchandise involved, you will likely be charged with a class A felony theft. There is possibility of jail time in light of this. If you have further questions, I practice here in NH and my email is firstname.lastname@example.org.
This charge would likely be a felony-level charge of Theft by Unauthorized Taking or Theft by Deception. A felony theft involves any amount greater than $500.00. This would be a class A felony as it is greater than $1,000.00. If the person has no prior criminal record, there is a strong chance that the result of the case would not end up in jail time. Please feel free to contact me directly if you would like to discuss this further, email@example.com
If you got a CWOF on a DWI charge in MA, it may be complicated to get your bus license reinstated. However, if this happened in NH (or if it's for a non-felony, non-driving charge), you shouldn't have much of a problem. Also, if this happened in H and the case was dismissed, you should seek to annul the record of your arrest.