An investor could conduct a series of rollovers, swapping Property A for Property B, then Property B for Property C, and so on while deferring any capital gains tax liability for years or even decades until they eventually dispose of an asset either through a traditional sale or through inheritance and estate planning.Opportunity Fund investments allow investors to defer paying capital gains tax on their initial realized capital gains, but unlike a 1031 Exchange, that tax bill has set due date.

HELOC, 401k loan, sibling or friend's self-directed IRA, some people use IRA rollovers for a 60 day loan.  

Here are my current holdings: $28K in Money Market Savings $13K Roth IRA $10K in Wealthfront (90% stock / 10% bonds) $3.5K in Betterment (90% stock / 10% bonds) $46K in Fidelity Rollover IRA - Me $20K in Fidelity IRA - Wife No debt.

Among 401k's that are not self-directed, either the old plan or the new plan may likely disallow the rollover.

Ken,What you need is to rollover your current retirement account into self-directed IRA or self-directed Solo 401k.

Another option is you could let it roll over to month-to-month lease, which would keep your property rented, but give you more flexibility to not renew if the late pays continue.

I assume if so, all taxes/capital gains from the first flip would roll over into the next and not require me to pay taxes?

Does the lease roll over into m2m or another term lease?

If I were to roll over 60K in gains over into a new property that cost 300K and sold it 10 years later for 400K I would only have to pay capital gains on 80% of 160K? 

Account ClosedI would consider a few options:1) If you want to invest in real estate with an end goal of retirement income, keeping it in a Self Directed IRA or 401k is a plausible option. 2) If you want to use the money now, there is a strategy called the Roll Over Business Startup (ROBS)- the steps are complicated, which is why you would have an expert handle it for you.