I think there's a difficult decision to be made between making decent money working 8 hours per week and taking the risk of leveraging your skills to bump yours

I think there's a difficult decision to be made between making decent money working 8 hours per week and taking the risk of leveraging your skills to bump yourself up a level in a data-entry operation. Lacking details, the first scenario seems more attractive to me. I would encourage the OP to develop another money-making operation on the side while he has some free time.