Legal Question in Criminal Law in Florida

My fiance is being charged with failure to register after we moved from destin fl to another county in florida. When we arrived here he contacted a lady at the sheriffs dept who informed him all that was required was for him to get his address changed with the dmv. He informed her that he didn't have the money to get it done but would still he went down and let them know where his new address was. The officer informed him that she would work with him to just get the id asap. We received a call a couple weeks later from our previous landlord informing us that a man from the sheriff's office was looking for him. My fiance immediately called the man to let him kno we had been in contact with the lady here. The gentlman had informed him that it didn't show an address change in his system so he then went back to the dmv and begged for them to give him a letter stating his new address. He then called the gentleman back to inform him that he had contacted them again. The gentleman then told him it was up to this county what happened next. My fiance was able to squire the plastic id three days later and informed the lady here in this county that he had done so. We thought everything was ok until three weeks later the lady officer showed up at our home to inform us that there was a warrant for his arrest in our previous county. She stated she did not know why and told him if he promised not to run she would not handcuff him and even allowed him to ride up front to the jail. Before leaving she said she would contact the officer in our previous county to see if she could release him because he had registered with her. He was still transported to our previous county and has been there for four months. He has been to court once and was offered two years imprisonment because of the points system he is facin five years. He did not take it. He has court in a few days and my question is do u think if he takes it to trial instead of take a plea do u think he has a good case. The lady informed his court appointed attorney that he didn't register here but she liked him and wouldn't file charges here and we have since found out that she no longer works in investigations and is now a deputy. Not sure if her demotion is related or not. The state has no proof that he didn't appear at the dmv when we arrived but in return we don't have the proof he did. Should he take a plea or take it to trial?

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