We use Monte Carlo simulations to explore the statistical challenges of constraining the characteristic mass ($m_c$) and width ($σ$) of a lognormal sub-solar initial mass function (IMF) in Local Group dwarf galaxies using direct star counts. For a typical Milky Way (MW) satellite ($M_{V} = -8$), jointly constraining $m_c$ and $σ$ to a precision of $\lesssim 20\%$ requires that observations be complete to $\lesssim 0.2 M_{⊙}$, if the IMF is similar to the MW IMF. A similar statistical precision can be obtained if observations are only complete down to $0.4M_{⊙}$, but this requires measurement of nearly 100$\times$ more stars, and thus, a significantly more massive satellite ($M_{V} ∼ -12$). In the absence of sufficiently deep data to constrain the low-mass turnover, it is common practice to fit a single-sloped power law to the low-mass IMF, or to fit $m_c$ for a lognormal while holding $σ$ fixed. We show that the former approximation leads to best-fit power law slopes that vary with the mass range observed and can largely explain existing claims of low-mass IMF variations in MW satellites, even if satellite galaxies have the same IMF as the MW. In addition, fixing $σ$ during fitting leads to substantially underestimated uncertainties in the recovered value of $m_c$ (by a factor of $∼ 4$ for typical observations). If the IMFs of nearby dwarf galaxies are lognormal and \textit{do} vary, observations must reach down to $∼ m_c$ in order to robustly detect these variations. The high-sensitivity, near-infrared capabilities of JWST and WFIRST have the potential to dramatically improve constraints on the low-mass IMF. We present an efficient observational strategy for using these facilities to measure the IMFs of Local Group dwarf galaxies. ; Comment: Submitted to MNRAS. 12 pages, 9 figures, plus appendix