Question

Which of the four fictional characters in this section—louis timothy, debora riedhauser, akachi, or jeremy shrimpton— had the easiest time surviving in colonial america?

Answer 1

Of the four fictional characters, I think that Jeremy Shrimpton had the easiest time in surviving Colonial America. 

Jeremy Shrimpton was a wigmaker. Wigmakers were in high demand in England  and Colonial America because of their expertise. The wigmakers unique skill and talent ensure them a large market for their products. So, it is safe to assume that Jeremey Shrimpton enjoys the prestige and sales of being a wigmaker.

The other fictional characters had the following designations in life:
Louis Timothy was a rice farmer.
Debora Riedhauser was house servant. 
Akachi was a slave.