Recent literature reviews of empirical models for long-term investment analysis in agriculture see gaps with regard to (i) separating investment and financing decisions, and (ii) explicit consideration of associated risk and temporal flexibility and (iii) taking farm-level resource endowments and other constraints into account. Inspired by real options approaches, this paper therefore develops step-wise a model which extend a simple net present value calculation to a farm-scale simulation model which considers time flexibility, different financing options and downside risk aversion. We assess the different model variants empirically by analyzing investments into hazelnut orchards in Italy outside of traditional producing regions. The variants return quite different optimal results with respect to scale and timing of the investment, its financing and expected NPV. The step-wise approach reveals which aspects drive these differences and underlines that considering temporal flexibility, different of financing options and riskiness can considerably improve traditional NPV analysis.