Let’s not go into market speculation from SALT and interest deduction effects.

If you wish to speculate on appreciation cash flow is generally traded off for the risk of greater returns someday.  

One strategy discussed in the book  that is a pure SPECULATIVE and not INVESTING is securing the right to purchase a condo or townhome in a small development prior to construction and then selling your unit once construction is complete with the thinking that once the structure is standing, a lot more people will be interested and you will be able to sell for more than the purchase price. 

While I in no way want to speculate on what market may or may not appreciate, I can speak to the burden of unloading your worst property.

Maybe it's all speculative at this point, but it sounds like people are saying that things are too hot right now and that a cool down is imminent.

In this peculiar market with scarcity of RE product availability, aggressive buyers with cash are frequently paying above market prices based on speculative trends. 

At that time, investors were speculative and grabbed control of available properties anticipating growth of 50-60k people on the island.  

I think that some or even a lot of investors at 1 point or another probably tell themselves 'JUST BUY SOMETHING' in part just to finally get into investing - the hope/speculation/risk they are taking on is that the appreciation of the property is going to bail them out of any -ve or break even cash flow situation...As for me, i am in the NW burbs of Chicago (10 mins from border to WI) and have not started investing yet as i am wanting to read/learn a lot first and come up with a plan.

Rules:1 - Don't Loose money2- There must be Cashflow (don't buy on speculation of future value)3- You can't get rich slow ( like in over 40 years via a retirement fund)I have six single families and two duplexes on my own.  

@Kyle JosephJust speculating, but STR rates may go up in the near future.