Deferred Sales Trust into a future 1031 exchange

[Amit M.]

Hi all. Someone with a dozen highly appreciated homes and condos that wants to sell them all off and roll it into a large NNN commercial property, has the challenge of timing, as its hard to sell 12 properties at one time to coordinate a 1031 exchange. Let's assume the person needs 1-2 years to optimally sell off all the condos (need to vacate them, some remodeling, market timing, etc. on 12 separate properties.)

So....would it be possible to sell the condos off individually, and put them in a Deferred Sales Trust (either one trust if you can add more homes to it as they are sold off, or separate trust entities if you have to).  And THEN, once you sold all your homes, can you use the accumulated trust to facilitate a 1031 exchange into one large commercial property? Of course they key is to be able to do this and DEFER all your capital gains (which would be substantial.) 

Let’s also assume that the seller is ok with not touching/accessing any of the principal in the trust (but would consider taking interest payments, etc. if they can from the trust; whatever can be done without compromising a potential 1031 exchange.) Is this strategy legally possible? Thanks. 

[Dave Foster]

@Amit M., the deferred sales trust and monetized installment sale are both marketed as alternatives to completion of a 1031.  Not really possible to combine in this event since the 1031 triggers with the sale of your old property and you only have 180 days to complete.  Once you've sold and placed the proceeds into a trust there's not going to be the opportunity to do another 1031 because the 1031 has to be the sale of actual real estate followed by a purchase of real estate.

One alternative would be to find the NNN seller who is willing to sell you TIC interests periodically over a year to a year and a half. Then when each of your assets sells do a 1031 into a TIC interest of the large property. You may be able to cluster enough sales together that you could get a large NNN owner to look at that scenario.