Or is it more of a "yes but low llikelihood" type of gamble?

In 90% of these amazon reseller plans you need to leverage offshore production to produce your product cheaply and that requires a huge time commitment and initial upfront cost.

All the time: people mismanage their finances, they neglect repairs, they gamble too much, they become hoarders.

The old adage about not gambling with more than you are willing to lose certainly holds true here.

Even after this, there are many more strategies that can be implemented (equity stripping, off-shore trusts, etc.,) but five is a memorable number.

Stock market is an investment, and as such is still a gamble.

Pretty safe gamble looking at what Boulder has done in the past, but ultimately a gamble none the less.

.), and look at a bunch of properties until you find one that meets more of your criteria than the others. 5 years is a bit of a gamble; if your timeframe was closer to 10 I'd feel more comfortable but that's going to be the case no matter where you choose to invest IMO.   

That is gambling.

The new owner moves production to his existing off shore plant.