MP, you're looking at it all wrong. While you may be correctly analyzing the liquidity of most of your assets, I'm reading you want to divest. Which may take 5-10 years. BUT, does even a conservative estimate of your overall wealth leave you with enough money to get through retirement? That is the question you dodge time in and time out. And it is the most important question for you to answer. IF you have enough, then why take on unnecessary risk?

If looking to pull the plug now or before all your assets are divested, you may need to do something else. But, if your funds aren't in place now, you probably aren't ready.

Your in a position to be in control of your life. You need to determine what your needs are and develop a risk/investment profile from that. Instead, you are developing an investment/risk profile and letting that drive your needs. It's backwards.

Your situation is unique, and doing what other people are doing most likely isn't applicable to you. Stop being being stubborn.

You're going to be horribly disappointed in my 401(k) because it is not at all complex. If you're looking for a golden key to investment, this won't be is. First some introductory comments: I work for a Fortune 50 company and my retirement savings plan is administered by ING. I do the investing for the family and my wife handles cash flow and banking. We set aside a sizable portion of our earnings for investment but most of it goes into taxable accounts because of the 401(k) contribution limits (currently $17,500/year if you're under 50 and $22,500/year if you're 50 and over). If I have to put money into taxable accounts, I'd rather put it into a place where I have more choices. Most of my taxable accounts are at Vanguard and T Rowe Price.

So as of COB yesterday, my asset allocation was as follows:
31.71% S&P 500 Index Iund
31.55% International Index Fund
31.81% Russell 2000 Index Fund
4.93% Company Stock

Bear in mind that this account is only 1 portion of my overall portfolio. My wife also has a 401(k), we both have Roth IRAs and of course, there are the taxable accounts referenced above. If I had my druthers, I'd be in indexed value funds but I don't have those options. The reason I'd rather rather have indexed value funds in a tax sheltered account is because I'd like more of my dividend income tax sheltered. But since that's not offered in the retirement plan, I make do with what is offered. I also have a defined pension plan with the company, which figures in to my overall retirement planning.

As for the two investment properties, we actually just fell into being landlords without having a plan. When we got married, my wife moved into my house and we rented hers out. When we purchased a larger home a couple years ago, we bought our home near the market low but didn't want to sell the house we were living in at similar lows, so we rented that out as well. It's worked out well for us, but we plan to sell both homes when property values recover somewhat. If that comes at a time when we no longer want/need separate offices, we might sell our present home as well and downsize our own living space.