The criticality of transformers and reactors in the power transmission network and the paramount importance of ensuring their reliability through maintenance of the insulating oil is known. This paper presents a comprehensive examination of the efficacy and economic viability of a dielectric oil regeneration system, as implemented by the Transmission System Maintenance Department (TSMD) of the Independent Power Transmission Operator (IPTO), Greece's sole transmission operator. Through a detailed chemical analysis and performance evaluation, we assess the impact of the regeneration system on treated insulating oil quality over multiple cycles. The study reveals that the electrical properties of the insulating oil are fully restored after regeneration, negating the need to fully replace it, while the investment becomes cost-neutral within weeks from the commissioning of the regeneration system. This economic analysis, coupled with the system's environmental benefits of reducing waste oil generation, positions the dielectric oil regeneration system as a compelling solution for the maintenance of power transmission assets.