Seeking book about baseline life planning and expectations

In an attempt to find useful “base rate expectations” for the rest of my life (and how actions I might take now could set me up to be much better off 10, 20, 30, 40, 50, 60, and 70 years from now) I’m looking for a book that describes the nuts and bolts of human lives. I want coherent discussion from an actuarial/​economic/​probabilistic/​calculating perspective, but I’d like some soulfulness too. The ideal book would be published in 2010 and have coverage of the different periods of people’s lives and cover different aspects of their lives as well. In some sense the book would be like a nuts and bolts “how to your your life” manual. Hopefully it would have footnotes and generally good epistemology :-)

To take an example of the kind of content I would hope for (in a domain where I already have worked out some of the theory myself) the ideal book would explain how to calculate the ROI of different levels of college education realistically. Instead of a hand-waving argument that “on avergae you’ll make more with education” it would also talk about the opportunity costs of lost wages, and how expected number of years of work impacts on what amount of training makes sense, and so on.

To be clear, I don’t want a book that is simply about deciding when, how, and for how long it makes sense to train for a job. Instead I want something that talks about similar issues that I haven’t already thought about but that are important, so that I can be usefully educated in ways I wasn’t expecting. My goal is to find someone else’s scaffold to help me project when and why I should (or shouldn’t) buy a minivan, how much to budget for dentistry in my 50′s, and a breakdown of the causes of bankruptcy the way insurance companies can predict causes of death.

I was hoping that the book How We Live: An Economic Perspective on Americans from Birth to Death would give me what I want (and it is still probably my fallback book if I can’t find anything better) but it was written in 1983, and appears to be strongly oriented towards public policy recommendations rather than personal choice.

Books that may be conceptually nearby that seem non-ideal include:

Dear Undercover Economist: Priceless Advice on Money, Work, Sex, Kids, and Life’s Other Challenges—My second place fallback because it covers real life content, is from 2009, and the first book in the series was pretty solid on economic theory. The problem is that it seems like haphazard coverage of the subject matter rather than “a treatise” that aims to describe the full ambit of life issues, sort them by priority, and deal usefully with the big stuff.

The Average Life of the Average Person: How It All Adds Up—Just a collection of factoids, like the number of cumulative days the average person spends on the toilette, the value add is the collection and the juxtaposition. Mere factoids might actually be useful as a list of things to think about optimizing for long term impact? Not what I want, but potentially relevant.

The ABCs Of Strategic Life Planning—The first problem is that this appears to be a workbook with questionnaires (presumed target market is people dealing with akrasia) rather than a narrative of fact and theory (giving the logical scaffold for a general plan). The second problem is that the marketing means it is probably from the business/​self-help genre from which I expect relatively little epistemic rigor.

The How of Happiness: A Scientific Approach to Getting the Life You Want—This book covers the “softer issues” that I definitely care about and don’t expect to be covered by economists. It seems potentially interesting, but in addition to not covering the other subject areas, it sounds more like a literature review of positive psychology results than like a “normal life overview”.

The Logic of Life: The Rational Economics of an Irrational World—It is good that this is recent (from 2008) but it is poorly reviewed, haphazard in subject, and full of shiny stuff that’s intended to be stimulatingly non-intuitive. I’m looking for meat and potatoes.

Hidden Order: The Economics of Everyday Life—Purportedly a lot of economic theory (which is not what I’m looking for) and then some shiny examples that Freaknomics later (it was written in 1997) made somewhat trendy. However, the title sounds like the book could have been close to what I want.

Can anyone suggest a book that is “a coherent overview of the intersection of these books and anything else I forgot”? There may be no book that matches my ideal, but I wouldn’t be surprised if something pretty close to it exists that I just haven’t found yet.

Help appreciated!