Forest cover transitions in the developing tropics are conditioned by agricultural change. The expansion, intensification, and diversification of agricultural land uses are tied to regional economic/environmental regimes and decisions of local farming households. Land change science and agrarian systems research share an interest in the drivers of household strategies, land use impacts, and typologies of those land uses/drivers. This study derives a typology of farming households in southern Mexico based on emergent patterns in their land use combinations and analyzes their household and policy drivers. The results reveal broadly diversified household land use portfolios as well as three emergent clusters of farmstead production orientation: (i) extensive subsistence-oriented conservationists, (ii), dual extensive-intensive farmers, and (iii) nonextensive diversified land users. Household membership in these clusters is uneven and strongly related to tenancy, land endowments, wage labor, and policy subsidies. Although most households are following a nonextensive agricultural strategy incorporating off-farm incomes, the likelihood of a regional forest transition remains debatable because of the disproportionate deforestation impacts of the less common strategies. Conservation development policies in the region need to accommodate diverse smallholder farming rationales, increase off-farm opportunities, and target sustainable development with the assistance of community conservation leaders.