If field goals were suddenly worth four points and touchdowns were worth five, football coaches would change their strategies. This type of scoring change has occurred in the estate planning field, but many people keep using their old playbooks.Recent income and estate tax updates have adjusted how the planning game should be played. If your estate plan was drafted before they came into effect, reconsidering how you structure your estate could save you tens of thousands, or even millions, of dollars.The Changing RulesTo understand these rule changes, we should rewind to the year 2000. The federal estate tax only applied to estates exceeding $675,000 and was charged at rates up to 55 percent. Long-term capital gains were taxed at 20 percent. Since then, the amount that can pass free of estate tax has drifted higher, to $5.43 million in 2015, and the top estate tax rate has dropped to 40 percent. On the other hand, the top ordinary income tax rate of 39.6 percent when coupled with the 3.8 percent Net Investment Income tax is now higher than the federal estate tax rate.Although the top capital gains tax rate of 23.8 percent (when including the 3.8 percent Net Investment Income tax), remains less than the estate tax rate, these changes in tax rate differentials can significantly modify the best financial moves in planning an estate. While estate tax used to be the dangerous player to guard, now income taxes can be an equal or greater opponent.Besides the tax rate changes, the biggest development that most people’s estate plans don’t address is a relatively new rule known as the portability election. Before the rule was enacted in 2011, if a spouse died without using his or her full exemption, the unused exemption was lost. This was a primary reason so many estate plans created a trust upon the first spouse’s death. Portability allows the unused portion of one spouse’s $5.43 million personal exemption to carry over to the survivor. A married couple now effectively has a joint exemption worth twice the individual exemption, which they can use in whatever way provides the best tax benefit. Portability is only available if an estate tax return is filed timely for the first spouse who dies.From a federal tax standpoint, if a married couple expects the first spouse to die with less than $5.43 million of assets, relying on portability is a viable strategy for minimizing taxes and maximizing wealth going to the couple’s heirs. Estate planning for families with less than $10.86 million in assets is now much more about ensuring that property is distributed in accordance with the couple’s wishes and with the degree of control that they wish to maintain than it is about saving taxes. However, state estate taxes can complicate the picture because they may apply to smaller estates.Below are a number of plays that families who will be subject to the estate tax should consider to optimize their taxes in today’s environment. Although many of the techniques are familiar, the way they are being used has changed.The New Estate Planning PlaysEmpowering Your Plan’s “Quarterback”A successful quarterback has a solid group of coaches providing him with guidance, but is also allowed to think on his feet. Similarly, the quarterback of an estate, the executor or a trustee, needs to be given a framework in which to make his or her decisions but also flexibility regarding which play to run. Today’s estate planning documents should acknowledge that the rules or the individual’s situation may change between the time documents are signed and the death or other event that brings them into effect. Flexibility can be accomplished by expressly providing executors and trustees with the authority to make certain tax elections and the right to disclaim assets, which may allow the fiduciaries to settle the estate in a more tax-efficient manner. Empowering an executor has its risks, but building a solid support team of advisers will help ensure he or she takes the necessary steps to properly administer the estate.Maximize the Value of Your Basis AdjustmentIt’s a common misconception that lifetime gifts automatically reduce your estate tax liability. Since the two transfer tax systems are unified, lifetime gifts actually just reduce the amount that can pass tax-free at death. Lifetime gifts accomplish marginal wealth transfer only when a taxpayer makes a gift and that gift appreciates outside of the donor’s estate. In the past, people generally wanted to make gifts as early as possible, but that is no longer always the most effective strategy due to income tax benefits of bequeathing assets.One big difference between lifetime giving and transfers upon death is the way in which capital gains are calculated when the recipient sells the assets. With gifts of appreciated assets, recipients are taxed on the difference between the transferor’s cost basis, typically the amount the donor paid for the asset, and the sales price. The cost basis of inherited assets is adjusted to the fair market value of the assets on the date of the owner’s death (or, in a few cases, six months later).When choosing which assets to give to heirs, it is especially important to make lifetime gifts of assets with very low appreciation and to hold onto highly appreciated assets until death. If a beneficiary inherits an asset that had $100,000 of appreciation at the donor’s death, the basis adjustment can save $23,800 in federal income taxes compared to if the beneficiary had received the same property as a lifetime gift. Unfortunately, the basis adjustment upon death works both ways. If the bequeathed asset had lost $100,000 between the time it was purchased and the owner’s death, the recipient’s cost basis would be reduced to the current fair market value of the property. Therefore, it is advantageous to realize any capital losses before death if possible.Holding onto appreciated assets until death is appealing for income tax purposes, but might not be advisable if the asset is a concentrated position or no longer fits with your overall portfolio objectives. For these types of assets, it’s worth analyzing whether the capital gains tax cost is worth incurring right away or if you should pursue another strategy, such as hedging, donating the asset to charity or contributing the property to an exchange fund.Choosing not to fund a credit shelter trust upon the first spouse’s death is a perfect example of maximizing the value of the basis adjustment. These trusts were typically funded upon the first spouse’s death to ensure that none of the first spouse’s exemption went to waste. Since the portability rules allow the surviving spouse to use the deceased spouse’s unused exemption amount, it is no longer essential to fund a credit shelter trust. Instead, allowing all of the assets to pass to the surviving spouse directly allows you to capture a step-up in basis for assets upon the first spouse’s death, and then another after that of the second spouse. Depending on the amount of appreciation and the time between the two spouses’ deaths, the savings can be substantial.Annual GiftingMaking annual gifts is a traditional strategy that remains attractive today. In addition to the $10.86 million that a couple can give away during their lifetime or at death, there are also some “freebie” situations where gifts don’t count towards this total. You can make gifts up to the annual exclusion amount, currently $14,000, to an unlimited number of individuals, and you can double this amount by electing to gift split on a gift tax return or by having your spouse make separate gifts to the same recipients.Transferring $14,000 may not seem like a meaningful estate tax planning strategy for someone with more than $11 million, but the numbers can add up quickly. For example, if a married couple has three married adult children, each of whom has two children of their own, the couple could transfer $336,000 to these relatives each year using just their annual exemptions. If the recipients invest these funds, the future appreciation also accrues outside of the donors’ estates, and the income may be taxed at lower rates.Contributing the annual exclusion gifts to 529 Plan education savings accounts for the six grandchildren can accelerate the gifting process and increase the income tax benefits. A special election allows you to front-load five years’ worth of annual exclusion gifts into a 529 Plan, which would currently allow $840,000 in total gifts to the six grandchildren. In this scenario, the grandparents would not be allowed to make any tax-free gifts to the grandchildren during the following four tax years. Since assets in a 529 Plan grow tax-deferred and withdrawals for qualified educational expenses are tax-free, you can realize substantial income tax savings here. If you assume the only growth in the accounts is 4 percent capital gains, which are realized each year, that results in about $8,000 in annual income federal tax savings per year, assuming the donor is in the top tax bracket.You can also pay a student’s tuition directly to the college or university, since these payments are exempt from gift tax. This exception applies to medical expenses and health insurance premiums as well, as long as payments are made directly to the provider.Given that annual exclusion gifts don’t impact the $5.43 million lifetime exemption, I recommend making these gifts early and often, but remember to give away cash or assets that have very little realized appreciation. The earlier you make a gift, the more time the assets have to appreciate and pay income to the recipient.Lifetime Charitable GivingEarlier I mentioned that you want to avoid giving away appreciated securities during your lifetime. The exception to that rule is a gift to charity. By donating appreciated securities that you have held for more than one year, you can get a charitable deduction for the market value of the security and also avoid paying the capital gains tax you would incur if you were to sell the asset.If you know you have charitable intentions, it is more effective to donate appreciated securities earlier in life, rather than at death, since doing so removes future appreciation of the assets from your estate.Using Trusts to Increase the Effectiveness of TransfersLifetime transfers to standard irrevocable trusts are no longer as appealing as they used to be, now that the estate tax rate is closer to the capital gains rate. Assets transferred to irrevocable trusts during the grantor’s lifetime typically do not receive a basis step-up upon the grantor’s death. Therefore, determining whether it is more appealing to make lifetime transfers or bequests in a specific circumstance requires making assumptions and analyzing probable outcomes.Nonetheless, funding certain trusts in conjunction with other planning techniques can increase the planning’s effectiveness. An intentionally defective grantor trust (IDGT) is one of the most appealing types of trusts for wealth transfer purposes, because the donor is treated as owner of the trust assets for income tax purposes but not for estate and gift tax purposes. A defective grantor trust is a disregarded entity for tax purposes, so any income that the trust earns is taxable to the grantor. By paying the tax on trust income, the grantor effectively transfers additional wealth to the beneficiary.Another popular strategy is for a grantor to make a low interest rate loan to a defective grantor trust. The trust then invests the funds. So long as the trust’s portfolio outperforms the interest rate charged on the loan, the excess growth is shifted to the trust with no transfer tax consequence.One of the common ways to cause a trust to be intentionally defective is for the trust document to allow the grantor to retain the power to substitute assets held by the trust for other assets. Assuming a trust has this provision, it is very powerful to routinely swap highly appreciated assets held by the trust that would not be eligible for a basis step-up with assets of equal value held by the grantor that have little to no appreciation, such as cash.Rather than funding a credit shelter trust upon the first spouse’s death, a surviving spouse might choose to receive all of the assets outright and then immediately fund an IDGT that includes the power to substitute assets. The trust’s income would be taxed to the surviving spouse, allowing for additional wealth transfer, and the grantor could use the swapping power to minimize the income tax cost of the lost basis adjustment.Any transfer technique, such as a grantor retained annuity trust (GRAT), that allows a donor to transfer assets without generating a gift is also valuable, since it helps preserve the lifetime exemption amount as long as possible, thus maximizing the assets that can benefit from adjusted basis.Finally, trusts can be useful for keeping assets out of your estate that never should have been included in it. For example, wealthy individuals should generally purchase life insurance through an irrevocable trust, rather than directly in the insured individual’s name. Life insurance owned by decedents is includible in their taxable estates. By creating a trust funded through annual exclusion gifts and having the trust purchase the policy, you can ensure that the estate tax does not take 40 percent of the policy’s proceeds.Avoid Paying Estate Tax on Income TaxWhile the term “income in respect of a decedent” (IRD) might be obscure, it’s important to understand it, since it’s one of the worst deals in town. IRD is income that a decedent was entitled to but did not receive prior to death. While unpaid salary and accrued interest are common examples, the biggest risks lie with retirement accounts and annuities.Retirement accounts, such as 401(k)s and traditional IRAs, are typically funded with pretax money and taxed on the decedent’s estate tax return at their market value on the decedent’s date of death. However, because these are pretax assets, the beneficiary ultimately has to pay tax on the income before receiving it. In a simple example, if a decedent has a $1 million IRA that is being taxed on the estate tax return at 40 percent in 2014, the recipient would also need to pay additional tax on withdrawals from the IRA when he receives it. Assuming no growth in the assets and that the beneficiary is in the top income tax bracket, taxed at a rate of 39.6 percent, the recipient would need to pay $396,000 income tax as a result of the bequest and the estate would pay $400,000 of estate tax. This results in a total tax of $796,000 from the $1 million of assets. Compare this with a taxable account, in which assets would have their cost basis adjusted to the fair market value on the date of death, so the recipient typically needn’t pay much, if any, income tax to access the assets. Therefore, the tax would only be $400,000 – about half of the amount applied to the IRA.The additional tax is a bit overstated in the example above, because the estate tax paid on the IRD can be an itemized deduction that is not subject to the 2 percent floor. Nonetheless, it illustrates the point that it is better to minimize IRD and the resulting double taxation if possible.It may make sense to take distributions from your own pretax accounts in certain situations, because paying the income tax during your life allows you to reduce your ultimate estate tax exposure. Converting traditional retirement accounts to Roth accounts can also help maximize the value of your estate. Most people will want to avoid annuities too, not only because of their typically high fees, but because they are treated as IRD and do not receive a basis adjustment upon the owner’s death.The right play for your estate plan has become even more specific to your situation: where you live, how you invest, your life expectancy, your goals and priorities, and your future life plans. With no one-size-fits-all answer, it’s important to run financial projections to understand both the income and transfer tax consequences of your choices, so you can determine the best moves for your situation. Make sure you have someone on your team that can accurately analyze what’s best for your situation and, above all, keep your game plan flexible.