The settlers at Jamestown faced many challenges. One challenge was dealing with unfriendly Native Americans. Because of this concern, the settlers felt unsafe venturing away from their settlement. This was a big concern because the settlers needed food. This brings us to a second problem which was the lack of food. The settlers at Jamestown didn't have enough food. Because they felt unsafe moving away from the settled area, shortages of food were a big concern. Many colonists died from a lack of food. A third issue the colonists faced was weather. One reason why there was a shortage of food was because the area was experiencing one of the worst droughts ever in this region. This made growing crops very difficult. In addition, the winters were brutal. Many colonists died from the hardships they faced during the harsh winter. The colonists faced many challenges while they were at Jamestown.
The English settlers at Jamestown faced many challenges, some caused by mistakes made by the joint stock company, the "Virginia Company of London" that financed the venture. Other mistakes by the settlers themselves upon arrival, doomed many to death in the coming months and years. Add to these mistakes, challenges of the climate, the geography, and the poor relations with the natives the first permanent English settlement almost did not survive.
The investors in England wanted a return on their investment and had instructions for the settlers that made that a priority rather than the long term safety, security and survival of the colony. Consequently, there was little done to prepare for their survival in terms of planting crops, digging wells, and cultivating better relations with the native population. The Virginia Company did not send enough skilled workers, either farmers or other craftsmen. There were lots of upper class "gentlemen" not accustomed to the rigors of manual labor whether in farming or otherwise.
Upon arrival the settlers were looking for deep water close to shore in which to dock the ships and a place that could be easily defended against a Spanish attack should they appear. As it would take some time to build shelter on shore, the ships would provide that safety and security from an attack either from the native population or the Spanish. The spot they chose was a very unhealthy area with mosquitoes carrying diseases, and no fresh water. Consequently having to drink the slimy (low tide) and brackish (high tide) water contributed to sickness and disease. Their failure to dig wells was a fatal mistake. A prolonged drought also contributed to the lack of fresh water for drinking and moisture for growing what little crops they did plant. The climate was also a major challenge as Englishmen were not use to the extreme Virginia heat and humidity as well as the harsh winters that had been occurring during those years.
The native population viewed the new settlers as a threat and except for a few years of peace, relations were marked by almost constant warfare, another challenge that almost doomed the colony.