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Insuring the life of the transferee is an available option; however, any connection of the life insurance policy to the private annuity will be deemed as a secured transaction.
A private annuity is a special agreement in which an individual (annuitant) transfers property to an obligor. The obligor agrees to make payments to the annuitant according to an agreed-upon schedule in exchange for the property transfer.
Thus, annuity payments to an annuitant who was outliving his life expectancy is taxed as ordinary income. Additionally, the annuity payment must be based on IRS actuarial tables and cannot be related in any way to the amount of income earned by the asset; otherwise, the asset will be included in the annuitant's estate.
Annuity withdrawals made before you reach age 59½ are typically subject to a 10% early withdrawal penalty tax. For early withdrawals from a qualified annuity, the entire distribution amount may be subject to the penalty.
Each annuity payment is treated as part tax-free return of basis, part capital gain, and part ordinary income until your entire basis is recovered. Once your basis is recovered, the entire annuity is treated as part capital gain and part ordinary income until you have surpassed your life expectancy.
As long as you do not withdraw your investment gains and keep them in the annuity, they are not taxed. A variable annuity is linked to market performance. If you do not withdraw your earnings from the investments in the annuity, they are tax-deferred until you withdraw them.