A decent place to start would be The Investment Answer, which is a pretty conservative, simple investment strategy. Then branch out from there. Most retirement planning software makes big assumptions about return rates and the linearity of markets; you need to make sure you're aware of that when using it. Most of them are based around Modern Portfolio Theory and the Efficient Frontier, so it's a good idea to be aware of that and its weaknesses.

So much of personal finance planning revolves around your personality type and desires; for atypical personality types it can be a bit tricky to fit yourself into generalized models. You definitely need to think seriously about stuff like how mobile you want to be, what your risk tolerance is, whether you have dependents, etc etc.