When I was in engineering school, we actually had seminars about this kind of thing, but that was a long time ago. But honestly, I'd look at getting a consult

When I was in engineering school, we actually had seminars about this kind of thing, but that was a long time ago. But honestly, I'd look at getting a consult with a financial planner. Something as basic as a one-hour talk with an Edward Jones rep would probably help you more than a ton of books & blogs.