I would provide the judge everything he requests as quickly as possible. When you meet with him be humble and accept responsibility for your actions. In some cases it is a good idea to obtain a certificate of relief of civil disabilities. An attorney can get that for you without much cost. But I wouldn't sweat this as a reason for denial. I've had students get passed with multiple arrests for drugs, DUI, family court matters, prior protection orderes and even simple assault (charges dropped or ACD). At PPA we have an attorney on staff to handle the sticky cases but your county is little far for him to make appearances.
I sit back and laugh reading some of the responses. Everyone has this misconception about NYS. They're confusing the state with NYC. There is no great conspiracy in NY to keep people from getting a permit. I've had ONE student denied in 12 years of teaching - thousands of students and we're just 45 miles from NYC. Just one, and he was a felon who actually thought he could slip through the system. NY is a discretionary state and may not issue unrestricted carry permits until the licensing officer feels comfortable with the applicant. After all, he doesn't know you. I received a call from a student this week to thank me for guiding him to an unrestricted permit. He was a new applicant but before asking for an unrestricted permit he took several classes (basic pistol, PPOTH Basic). The judge was pleasantly surprised that he took the time to understand the sport and the laws. He was granted an unrestricted permit in Ulster County right from the start. The judge advised that he doesn't nromally do this but was pleased with this student's attention to safety and rule of law.
The permit process in NYS can be daunting. Not because of an anti-gun sentiment, in fact most upstate counties, bar a few, are pretty gun friendly. Upstate NY is mecca of huting for deer, bear, turkey and waterfowl. The upstate economies thrive on it. Many hunt with revolvers. Guns are present all around and during hunting season one can hear near continuous shooting from the wooded areas. The permit process can take from 3-9 months, depending on the county workload. In large counties like Orange their are only two people working in the permit department and they're swamped. However, in Orange County nearly 10% of the population has a CCW.
As a discretionary state, NY licensing officers like to see a period of good behavior with a firearm before lifting restrictions. This is a pain in the rear but can usually be accomplished. One must show the judge responsibility, attention to the rule of law, education in personal protection both inside and outside the home and sound principals of concealed carry. One obtains these credentials by taking appropriate NRA sanctioned classes or attending courses at a well known shooting academy.
Now NYC? Well, what can be said? 8.5 million people, mostly demcrat/liberal, comprising nearly 30% of the state population and consisting of numerous immigrants who vote liberal democrat. Anything for the promise of an entitlement or safety. It's very hard to beat the voting block in statewide elections, but thus far we've done pretty well. We have no laws against carrying in bars, restaurants, churches, local parks, cities other than NYC, state lands, public transportation, banks, etc. Only seen one anti gun sign in my life and that was at HSBC bank [I guess the robbers will use th drive up window ;-) ]. So all-in-all, considering the demographics of the voting population, we've faired pretty well thus far.
Several years ago a new family moved up from NYC. My neighbor was shooting on his property. The police were summoned to a call of a madman in the woods with a gun. When they arrived an realized who it was they all laughed it off. They had to explain to this hysterical woman that she's moved to gun country and to expect to hear shooting all around her. Her husband perked up and asked, "you mean I can have a handgun up here?" In NYC , the thinking is that gun = crime.
He was my next student. Today he and his wife both enjoy shooting sports and have joined the local fish an game club. She has become quite proficient with her Ruger mark IV.
Nothing feels better than watching the evolution of a convert.