Think the answer is to check all the records as you have been doing. I have done some work in the Sullivan land records in Monticello in the County Clerk's office. Think the oldest records do go back the the start of the county. Without trying to find my notes, think the earliest I found that helped be were either 1810 or 1811. I have also been to Kingston (Ulster), but don't remember that I had much time to work there.
According to the Handy Book, Orange County clerk has marriage records from 1908-1933, divorce and civil records from 1852 and land records from 1703 and census records. This may help you. Best of luck.
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