Why Was Charleston So Difficult to Settle? Many people were trying to settle in Charles Town. The people were looking for a new life. It was difficult to settle in because of geography, disease, and resources. The word “settle” means to adapt to a better life style. People wanted to settle in Charles Town for the land but, there were already natives there. So they settled in Charles Town anyway. Charles Town was difficult to settle because of geography, according to document A the settlers wanted land, soil ,and and the location. The land was good for growing crops and farming. The water was a advantage and a disadvantage it was a advantage for traveling and growing crops. It is a disadvantage because of flooding and could