Small business owners (SBOs), specially women, face several challenges in everyday life, especially when asking for microcredit loans from financial institutions. Usual difficulties include low credit scores, unbaked situations, outstanding debts, informal employment situations, inability to showcase their payable capacity, and lack of financial guarantor. Moreover, SBOs often need help applying for microcredit loans due to the lack of information on how to proceed. The task of asking for a loan is a complex practice, and asymmetric power relationships might emerge, but that benefits micro-entrepreneurs only sometimes. In this paper, we interviewed 20 women entrepreneurs living in a low-income community in Brazil. We wanted to unveil value tensions derived from this practice that might influence the design of AI technologies for the public. In doing so, we used a conversational system as a probe to understand the opportunities for empowering their practices with the support of AI multimedia conversational systems. We derived seven recommendations for designing AI systems for evaluating micro-business health in low-income communities.