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Makinde stated in June 2019 that he had met a debt profile of roughly ₦150 billion on taking office from Senator Abiola Ajimobi, while Debt Management Office and NBS figures put Oyo State's total debt at around ₦126 billion as of March 2019 — itself a heavy load relative to the state's revenue base at the time.

The administration grew internally generated revenue substantially over its first term and pursued a mix of debt service and new, more targeted borrowing for infrastructure. The state's debt profile and debt-service costs remained a live point of political dispute years into the administration, including a public disagreement with the state's own Attorney-General over unpaid contractor debts.

The Nigeria Union of Pensioners had sued the outgoing Ajimobi administration over ₦42.3 billion in unpaid gratuities and pensions owed to retired primary school teachers and local government staff, with a court ordering monthly payments of ₦250 million toward the arrears — a pace far too slow to clear the backlog within a reasonable time.

Makinde increased the monthly gratuity allocation after taking office — reported at ₦500 million shortly after inauguration and around ₦1 billion monthly in later years — donating his own salary to the fund and accelerating payments to retirees. Pensioner advocates credited the reform as a major improvement, though the full historical backlog was not immediately eliminated.

Years of heavy recurrent spending and debt service under the previous administration had left limited fiscal room for new capital projects, with many planned road and public infrastructure works stalled or abandoned at the point of handover in May 2019.

The administration introduced the Alternative Project Funding Approach (APFA) to unlock infrastructure spending despite constrained direct budget resources, and delivered a range of road and public works projects across the state. Large sections of rural road network remained in poor condition through the first term and into the second.

By 2019, kidnapping, armed robbery, and rural banditry were rising across the South-West with no dedicated regional security response — policing remained an exclusively federal responsibility under the constitution, and individual states had no legal framework of their own to organise supplementary community security.

Makinde joined the other five South-West governors in establishing the Western Nigeria Security Network (Amotekun) in January 2020, and signed Oyo's enabling legislation into law that March, operationalising a 1,500-officer corps by November 2020 — a genuinely new regional security institution, even though insecurity in parts of the state, including the 2026 Oriire abduction, later showed its limits.