You will be able to indefinitely defer all of the capital gains taxes as well as not have to recapture any depreciation.

And then you will purchase a new investment property and all of the gain is tax deferred indefinitely as @Jaron Walling said.The way to combine and get both advantages would be to move out and turn that property into an investment property for a year. 

Youtube is great - you can learn many different things from what neighborhoods look like, how to fix a part on car, make a certain type of dish/meal, understand a concept..etc

And defer the depreciation recapture indefinitely (if you continue to do 1031 exchanges and cost seg over and over)

Fortunately, we are in position that we can indefinitely absorb the reduced income that our STRs are producing.Good luck

But in any event, that trade-in value will be WAY BELOW top retail dollar he could get if he could afford to list it on cars.com and wait indefinitely to get a top dollar on well maintained, reliable car of the same size and year of make.   

A partnership can do 1031's indefinitely, so no issues with 1031s in the future if you go this route. 

And the rest can be deferred indefinitely in a 1031 exchange. 

It's about creating a reliable income stream that sustains your lifestyle indefinitely.

You cannot extract from it indefinitely; there is a limit to the number of properties you canpurchase in this manner without paying back into the life insurance which does not exist on a true 100% LTV.