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Mac software: quicken's worked for me. Not fancy, not pretty, but effective.

Talk to a professional about investing & protecting your assets. As you can live on the interest, perhaps the free time is more important than the money for now?

Sounds like a good time to invest in yourself. First: a small vacation (a few weeks, ~$2-5k) to really relax. Next: maybe some school if there were other things that piqued your interest before, but never had a chance to study. If not school, maybe not a bad time to just pick up some books and hedonistically blowing weeks on whatever you want to study :-) If anyone asks, call it market research.

Congrats!



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