Hi Case58 --This is a personal perspective here, but let's start with a question, rather than an opinion: What is your goal?With "several million", you can live comfortably, even in higher cost parts of the country, without needing to rely on esoteric optimization strategies.If you begin with your goal and build a strategy that would invest enough to meet your goal plus a comfortable margin, even within the constraints of today's market conditions, then what you'll likely find is that you'll still have cash left over. That additional cash can either be an additional buffer to help you sleep at night, additional money to put at risk in the hope of better returns or income, the 'splurge' on yourself and your family as a reward for a successful career and decades of hard work, or some combination or each.Ultimately, it's your choice, and you need to balance the financial concerns with the personal ones and decide on a solution that fits your personality and goals. No amount of wrangling over the edges of "should I invest now" or "should I wait until next month" or "should I ease in over time" is going to help if you're not comfortable with the fundamentals of your chosen strategy and how it helps you meet your goals.What you may want to do is take a free trial of the Fool's "Rule Your Retirement" newsletter, which can be found on a link on this page: http://www.fool.com/shop/newsletters/index.aspx . What you'll find there is a wealth of information on how to manage the transition from paychecks to living off your investments.Regards,-ChuckInside Value Home Fool
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