Well-being analysis (WBA) encompasses deterministic and probabilistic measures to capture the comprehensive status of power system fitness with regards to ensuring adequacy. A key application is to be found in reserve allocation studies, both in the regulated and the liberalized scenarios. This paper presents a revised WBA approach applicable to the determination of reserve requirements at the Hierarchical Level I (HLI) (generation systems) of bilateral contracts market. Heuristic modification factors are proposed for a resourceful deployment of the traditional WBA. This is done with a view to overriding the odds of strict optimistic appraisals or lenient pessimistic appraisals, whose resultant implications in the planning and operation of power systems might yield insufficient contingency measures or unwarranted redundancy. Further, as in the risk management methods used in financial and insurance industries, the risk metric value-at-risk (VaR) is employed in this paper for deciding the beneficial reserve levels to be engaged by potential customers in bilateral contract markets.