This paper presents risk prognosis methods for decision support in long term-asset management by quantifying how different classes of reinvestment strategies influence the reliability of supply. The reinvestment strategies we consider are age based, condition based and risk based, where risk is quantified in terms of expected energy not supplied (EENS). The risk prognosis model combines power system reliability assessment with simulation of the time development of components' technical condition. The condition of the component population is influenced by three different factors in the model: degradation due to aging, forced replacements due to non-repairable failures, and preventive replacement according to the given reinvestment strategy. In demonstrating the methodology we focus on transformers and utilize an existing transformer end-of-life model. An important secondary objective of the work is to quantify the uncertainty in the end-of-life model, and include this uncertainty in the risk prognosis. We show that although there is substantial uncertainty in the end-of-life model, the relative performance of the reinvestment strategies is easily identified. The risk based strategy is seen to outperform the age-based and condition-based strategies giving considerably lower EENS and uncertainty over time.