Question by Arthur: How is an Income Stream from a Structured Sale Taxed?
I have been reading up on how a structured sale works and would like to know just how I am taxed with this deferred instrument? It seems to me that instead of paying capital gains tax on my profit now, all I am doing is receiving a personal income stream (guaranteed, safe, secure, and with interest) over a certain period of time, but I will be taxed yearly for it on a personal income tax basis (which maybe higher than 15%). Am I mistaken?
Best answer:
Answer by VKJ
Your question caught my eye because I have not previously encountered the term “structured sale”. So I looked for something on the web and found an explanation. I’m not going to name the source because I don’t want to get embroiled in a lawsuit over what I’m going to say about this kind of transaction.
The transaction is described as a “guaranteed” installment sale. But the description states that the payment by the buyer is secured by an annuity from a large insurance company. And the tax treatment of an installment sale and an annuity are different in significant respects.
With an installment sale, any gain from the sale is only taxed as the payments are received. Part of each payment received by the seller is treated as a return of the (adjusted) cost of the property, part is usually treated as a capital gain and part is treated as interest income.
But if the installment obligation of the buyer is exchanged for an annuity issued by an insurance company, I suspect the IRS would treat that as a taxable disposition of the property for the seller. Even though the seller is still getting paid over time, the payments are now secured and it is the lack of security that is the basis of a deferral in an installment sale.
Some people argue that capital gains taxes can be deferred with a transaction known as a private annuity. A couple of years ago, the IRS issued a proposed regulation that was intended to eliminate the tax deferral. At least one tax professional claims that this regulation has been rescinded but I’ve not been able to confirm that.
But that really doesn’t matter because even if a private annuity still offers tax deferral, the deferral is lost if the buyer is an insurance company.
If I were seriously considering the use of this arrangement, I would insist on seeing a “covered opinion” or a “marketed opinion” by a well qualified tax lawyer. Those are terms of art in the tax business and they provide some insurance against penalties for following the advice in the opinions.
This is only a very brief reply involving some potentially complicated tax rules. Entire books have been written about the installment sale, and about annuities.
VKJ
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