The answer is always no. IRS regulations don’t allow transactions that are considered “self-dealing,” and they don’t allow your self-directed IRA to buy property from or sell property to any disqualified person, including yourself, certain family members, and others.

Advantages of Self-Directed IRAs The key advantages of a self-directed IRA are: Greater flexibility in the investments you’re able to hold in the account. Built-in tax breaks on the earnings from your investments. The opportunity to make investments that line up with your passions, knowledge or experience.

Disqualified persons include the IRA owner’s fiduciary and members of his or her family (spouse, ancestor, lineal descendant, and any spouse of a lineal descendant). The following are examples of possible prohibited transactions with an IRA.

Tax benefits of a self-directed IRA In a nutshell, money you contribute to a self-directed IRA may be deductible on your tax return, depending on your income and whether you or your spouse have a retirement plan from your employer. With a Roth self-directed IRA, contributions aren’t tax-deductible.

Your self directed IRA can have a wide variety of assets that generate income. For example, interest earned, dividends, royalties, and pensions. In a self directed IRA, these are taxed in the same way as other IRAs that generate capital gains.

If your IRA owns an LLC 100%, then it is disregarded for tax purposes (single-member LLC) and the LLC does not need to file a tax return to the IRS. If your IRA incurs Unrelated Business Income Tax (UBIT), then it is required to file a tax return. The IRA files a tax return and any taxes due are paid from the IRA.

Self-managed IRAs are offered by big brokerages and online trading firms like E*Trade and Charles Schwab and let you choose the stocks, bonds, mutual funds and treasuries to invest in.