Hi Kathie! I have been studying Jamestown recently myself and hope I can offer some help. Jamestown, Martin's Brandon, Martin's Hundred, and others were settled by Adventure Merchants of England granted by King James I. Taking a closer look at what was happening at the time, especially at Martin's Brandon, where at least John Martin was travelling back and forth from the colonies to England quite frequently, on one occasion to obtain a better patent, and another to defend his patent. His Martin's Brandon Plantation on the James River down the river from Jamestown caused issues, ranging from problems from the neighbors about what kind of people were living and associated with the property, to his business associate, George Bargrave (Bargrave-4) using his extensive trading charter patent to bring in the first slaves to America.
In order to make sense of the records available, it really makes sense also understand the people, the time, and the situation going on: These people were wealthy merchants, and in many cases, Captains. Where you see "Captain" and the Virginia Company, just know you are looking at THE world travelers of the day, who also went to Bermuda Trinidad and Jamaica amongst other places, and certainly went back and forth to England, mostly for business purposes, only to sail off again. To find the the records, you have to know what you are looking for so you know it when you find it. In this case you are looking for candidates in Jamestown with the ability to sail back and forth: John Martin, John Smith, and John Rolfe to name 3.