For those just getting their feet wet in real estate investing, picking that first property can be a knee-knocking experience. Of course, the objective is to make your choice based on purely economic parameters. But clearly, when it comes to taking a risk with your own hard-earned money, that can be easier said than done.

Many times, when it comes to deciding between Property “A” and Property “B,” emotions will take over and attempt to dictate what you should buy. Many novice investors indignantly declare, “I refuse to purchase any building that I wouldn’t live in.” If you recognize yourself making that statement, you should realize that you’re on the verge of leaving lots of great opportunities behind for someone else to discover.

But don’t fret, you are not alone. In fact, it’s easy to see why emotions rule the day—you’re fearful of losing what little money you have been able to save. In fact, many will argue that the fear of losing their nest egg is as much (if not more of) a motivator as is the promise of gain from investing it. To illustrate, let’s say you were invited to a get-together at 9 PM to learn about a business opportunity that could very well make you $1,000 on a $5,000 investment. After a bit of thought, you might decide to spend that time watching the news or Seinfeld reruns on TV instead. But let’s turn the tables: What would happen if you got a call and were told you would lose that $1,000 if you didn’t go to the 9 PM meeting? Precisely.

There is no shame in a bit of apprehension. In fact, playing the devil’s advocate will usually help you make prudent decisions along the way. But beware unfounded fear about losing money by buying the “wrong” building could very well keep you from obtaining just the perfect fit for your long- term plan. Thankfully, unlike investing in commodities such as stocks and bonds via the advice of a so-called expert, there are concrete things you can do in this game that will minimize the risk of ever overpaying for a building, namely, learning how to value property accurately for yourself.

Expert help is nice, but when it comes to protecting your own nest egg, the peace of mind that will come from conducting your own analysis will be nothing short of invaluable.

There is one more technique to avoid paying the taxes due on some of the profit from your real estate. This is by securing new financing to pay off the existing loan and net additional cash at the closing because of the increased value of the property. If you are still in the equity-building years of our plan, you will probably use that money to acquire an additional property. One of the great advantages of getting at some of the profit using this method is that there is no tax due on the money. Because we “borrowed” the money from the bank, we have to pay it back, and therefore, not only do we not have to pay any tax, but right now we can write off the interest as a deduction on the property.

Owners who have properties that are managed particularly well prefer this technique. What’s more, if you’ve managed your property correctly, the increased rents should more than cover any increased mortgage payments. If you are in a market where you can pull out most of your equity to move into another property and still keep the original property, you could be well on your way to creating a comfortable retirement scenario for yourself.

To sum up a long and complicated chapter, this information is designed to give you a basic understanding of real estate taxation and some tax-deferral methods. The goal is to make you aware of the complexity of this area so you will seek the advice of your tax expert before you make any move. When it comes to taxes, even minor mistakes could be costly. To that end, we recommend the following.

First, before you ever list a property for sale, make sure you schedule a general review meeting with your tax consultant. Review your goals, discuss all the alternatives, and get a general idea of your position. Second, when listing a property for sale make clear to your agent and in the listing contract that any transaction must be reviewed and approved by your tax consultant. And, finally, when negotiating a potential sale or exchange, include a contingency that gives you a right to have the final purchase agreement reviewed and approved by your tax consultant. This will give you an out if your tax expert advises you against the transaction.

While no one makes it a goal of their life to owe child support or alimony, you can often find yourself owing significant amounts of money due to someone else’s decisions. Because there is often a mountain of emotions tied to these debts, they are some of the easiest to negotiate and find a compromise that works for both parties.

The legal system and states have become increasingly aggressive in pursuing people who fail to pay what they owe. Because of this increased aggressiveness, failure to pay child support or alimony can lead to garnishment of your wages and a debt that follows you even if you declare bankruptcy of move out of the country!

Like legal and medical debts, proactive negotiations can often reduce or even eliminate amounts you owe to other parties. Hence, if you find yourself in this situation, you need to put it at the top of your prioritized list.

The first major risk management tool was insurance. The insurance industry had its origins in the ancient practice of bottomry, in which the owner of a ship borrowed money for equipping the vessel and, for a definite term, pledged the ship as security. If the ship was lost in the specified voyage or period, the lender (insurer) lost his money. Clearly, a rich lender had opportunities for diversification unavailable to the owner of a single ship. Bottomry is virtually extinct today, although the maritime insurance business (which lacks the lending aspect) that replaced it is alive and well. Bottomry was a remarkable development because the risk to the lenders could still be very significant in view of the massive potential losses from a single storm or pirate, whereas the ability to diversify these risks could be limited to the commercial fleet operating out of a single port. Interest rates must have reflected these risks.

The underwriting of accidental risk became an important business in 1771, when 79 underwriters pooled their activities and created the original Members of Lloyd’s. They would appear to have intuitively understood the value of diversifying their risks.

Benjamin Franklin set up the first American insurance company in 1752, writing fire insurance. Since then, a massive global insurance industry has developed to handle a host of relatively small risks whose occurrence is statistically predictable: Health and dental insurance, life insurance, fire and flood insurance, and automobile collision and liability insurance are examples.

These instruments are familiar because they work their way into most household budgets.

Modern risk management depends absolutely on modern mathematics. 7 In its absence, the ancients were as handicapped as mariners without a compass. The introduction of modern arithmetic allowed thought pioneers such as Cardano and later Galileo to develop the theory of combinations—essential for figuring the probability of outcomes when rolling dice or drawing cards. Here the modern concept of probability was born.

Though useful at the gaming table, probability theory was still not very useful for real world events. The theory of statistics was needed for that, and the first statistician might have been a Londoner, John Graunt, who studied the age distribution and the causes of death from bills of mortality in London parishes.

The primitive database (i.e., the church records) from which Graunt derived his study was itself an innovation and was less than 60 years old at the time of Graunt’s study, published in 1662. Databases would go on to become a powerful source of wealth and value, but that is another story. The astronomer and mathematician Edmund Halley extended Graunt’s work into an analysis of life expectancies, creating in 1693 a scientific basis for the valuation of annuities. Still, it would take nearly another century for a modern life insurance business based on actuarial data to evolve.

From a mathematical viewpoint, the remaining big step was the discovery of the bell-shape curve. Abraham De Moivre in the 1730s, using the binomial theorem,8 developed the concepts of the normal distribution and the standard deviation, the latter being a measure of the dispersion of the distribution about the mean. In Chapter 5, we relied on his formula, coded as NORMSDIST in the Excel spreadsheet program, to calculate Black-Scholes option values! And how did we calculate volatility? We used De Moivre’s formula for the standard deviation.