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.