Yet, I'm willing to gamble on the fact that more often than not, they're the same ones who are unhappy about their experience.  

Other than that its more of a gamble when it comes time to flip.

Buy and hold near downtown Hyannis is a gamble but probably the best deal you will find on the Cape.

@Einar Mykletun, even though I don't normally recommend investing for SPECULATIVE appreciation, I did give Thomas S. a vote for his post which partly reads: "since you provide no specifics on individual properties, I would say by all means continue to speculate on appreciation".The main reason I gave that vote is because Greg went on to write: "But beware the time may be approaching soon to liquidate as they are most likely not self supporting investments regardless of your present perceived "positive cash flow"".Nothing that I've seen you post so far has led me to think that you give as much thought to an EXIT strategy as you do to your "one day it SHOULD cash flow positively" philosophy.It's nice to have the income where you can keep going into those gambling halls night after night, month after month, year after year, HOPING that a 0.67%/m gross return on your "investment" will magically mean ACTUAL cash flow, without you ever selling anything!

But much like the stock market, you're gambling on an Apple or a Google, and may end up with a Theranos;) If you diversify, and one of the deals goes south, your losses will be offset, and you can get out and move into another deal.

At the end of the day, an investment is nothing more than a gamble.

If you are a gambling man, offer the birddog $500 for the deal, or write out some contract that says you will give him $100 for the lead and $500 more if/when it closes.  

Good growth Looks like Coolidge was able to secure proctor and gamble to build their manufactured plant.

Anything before is pure gambling.

@Sheila Villacampa I understand the long term gamble/play your taking.