A large volume of literature discussion focuses on the weakness of sub-Saharan Africa land use planning systems to the exclusion of their benefits. The starting point to any effort at assessing the extent of benefit of these land use planning systems is to devise a suitable benefit estimation methodology. This study based on a review of the literature interrogates the conventional quantitative methodologies usually employed in the developed world to calibrate benefits of planning policies. It is established that conventional methodologies used in the developed world are associated with complexities and require huge volumes of organised data, which are hardly encountered in sub-Saharan Africa. This signifies that a bespoke methodology is required to estimate the benefits of planning regimes in the sub-region. The study, therefore, prescribes a methodology based on the nature of planning regimes and organised data peculiarities in the sub-region.