One of the best way to hurdle the brick walls in my research is to look at the family and friends of my ancestors. By looking at other family members you can find clues that may lead you on a path to where you want to go. Examining the neighbors, friends, and associates of a ancestor can also point the way as well as finding new areas of research. Here is an example of what I did with a will.
When Captain James Peters wrote his will in August of 1802, he was suffering from yellow fever. A huge epidemic swept through New York at that time and sadly, at the age 41 he was a victim of the disease. When his will was probated not once, not twice but four times, the original and copies of it were made. These copies had to be accurate because it was a legal document. The fact that he was a sea captain and was wealthy according to the standards at that time made his will an important business document.
According to his will his executors were William Seaton of New York City and John Woodward and Job Tabor of New London. William Seaton died in Italy shortly after leaving New York for a better climate. (Yes, he was Mother Elizabeth Seaton's husband!) Job Tabor was forced into bankruptcy in 1804 and by 1806 had died. The surviving executor, John Woodward, advertised in both New London and New York City newspapers that he was the surviving executor of James Peters. He also died before the probate could be completed because by 1809 Guy Richards of New London had petition in New York City courts that he was guardian of Captain Peters' son, James, and asked to be named the executor of Captain Peters' will.
On my "to do" list, I still need to examine William Seaton's and John Woodward's wills. I did look at the bankruptcy records for Job Tabor (located in NARA in Waltham). On a hunch I decided to also look at Guy Richards' will and lo' and behold there was James Peters Junior listed. This lead me to other records in other locations including tracking down James Peters Junior's will in Philadelphia and discovering more records for me to examine.