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.
Thanks I'll pick up the book and try and shoe horn my odd desires in.
Does anyone have recommendations for software or articles on how to plan your financial life?
Lets say I have a goal, retire at age 50 to X location with Y income in todays currency. Are there any tools that help me make decisions? E.g. to rent for a while, until a property dip (based on cyclical observations). Or how to spread investments over countries and investment types to mitigate black swan events like economic collapses.
I found reno when googling. But I don't know whether thats just because they are good at SEO or actually useful for what I am suggesting. Preferably it would have a wealth of data, such as property price increases by location etc.