tax and capital gains strategy for a retiree

[Account Closed]

I have a neighbor down the street ask me how he could sell his 4 investment properties and not have to pay any capital gains tax. I thought do a 1031 like kind exchange but he is 75 years old and wants to liquidate his assets and put the cash in the bank. I would like to approach him with some solid options as I would like to have an option to buy his properties. 

Option 1: He 1031's all properties into something like or kind in value, treats it as an investment but after 6 months moves into the newly bought home for two years before selling. Not sure if he can make the move into an investment house and call it an owner occupied home or for how long it takes to qualify as an owner occupied. 

Option 2: We work to a seller financing deal to keep him getting paid but as his houses are free and clear he is already getting paid pretty good so the only value I see in that is that they wouldn't be his worry anymore. What if we did seller financing I fixed up the houses for a year and then put them on the market and paid the guy off. Is he still liable to pay capital gains on that money since the home notes are in my name at that point? 

Option 3: Whats the word from BiggerPockets? 

[Steve Vaughan]

I have a 95 yo seller I am working on who is facing the same thing.  Wants out of the day to day, likes the monthly, wants his heirs to inherit tax-free.  Since the estate tax exemption was recently doubled, he thinks he'll sneak in just under the $11M max.

I offered a 3yr lease with option to buy (LO) or a Master LO (MLO).  Option Consideration in the the form of property taxes as they come due twice per year.  Extendable every 3 yrs.  He was like wait- can i still deduct the property tax payments?  I would I said.

I was close, but didnt get the deal. He did chuckle and say it's the most creative offer he's ever seen though.  At our annual lunch (5 yrs now) I'll re-present making the Option not exersizable until his passing.  That may do it.  

Try an extendable MLO that you won't buy until in his estate.