Erring on the side of caution and conservative estimation is usually a good thing. And within the next few weeks, I hope to be implementing a Monte Carlo simula

Erring on the side of caution and conservative estimation is usually a good thing. And within the next few weeks, I hope to be implementing a Monte Carlo simulation mode which should help to account for the fact that many of these variables really follow their own distributions. Hopefully this will help make it clearer what the chances of success are given a broader range of scenarios, events like market crashes or longer downturns, etc.