So I said its probably best to just pay the tax.If an investor overpay a ton, just to save on taxes, most likely they'll be inflicting significant financial damage to their portfolio… it’s probably best to opt out and pay the tax.1031s aren't structured in a way that makes someone "overpay" - it mainly comes down to poor planning which puts them in that situationNever let the tax tail wag the dog!

Guess that sales rep caught you by the tail.

Properly executed, an investment in these types of property can garner substantial passive losses, often equal to the amount of capital invested (or more) even in years where the benefit begins to sunset.A few words of caution: - Be careful not to let the "tax tail" wag the dog.

Those same people are now left with their tail between their legs as not only are they not getting 18% they are losing 50-100% and will take a close to a decade to recover those funds. 

I would say that you are looking to grab a Gator by the tail!

Its not even being the tail of a dog, its more like being a flea on the tail of the dog. 

I don’t think there is a clear answer here because you’d have to compare a specific property to potentially an entire asset class, when I buy the s&p I’m buying 500 stocks, when I buy a bond I’m buying a yield but each property is its own deal, what I will say is I think on average real estate is incredibly overrated asset right now (with the caviot that I do think the U.S. debt situation has some significant tail risk long term, and real estate is probably the best hedge against that) but I think to me it’s very basic in pretty much any market you are looking at even with 20% down significant negative cash flow, with housing so unaffordable it seems unlikely we have a ton of appreciation going forward, I can keep my cash liquid and still get over 5% risk free in a moneu market fund with zero effort or risk, I can invest in 500 great companies who can innovate there way to more profits, vs real estate which for better or worse is more of a fixed asset, I also have this theory that since anyone with extra money sitting around or a 401k just throws it into the market you can end up with higher multiple’s than you’d otherwise think vs housing which is again much more set by affordability than sticking some extra money in the market, all that is to say unless I find a deal that has above average returns I’d rather just collect money from some mix of stock and bonds vs paying money each month for the privilege of owning a property that may or may not go up in value.  

I say you are not even the tail of the dog but a flea on the tail of the dog. 

They responded by calling me a tattle tail, said that I was way out of bounds and now, 4 months later there is a non working boat, a crashed car and numerous piles of dog poo in the yard.

. - double tap: less than 30 minutes if repaired via a pig tail.