But, I'm not a gambler. 

Are you a gambler or an investor?

But each transaction is a roll of the dice, and as any gambler knows if you continually “double down” it’s just a matter of time before you lose your “stake”. 

A friend who is a bookie and gambler once told me lessons aren't cheap. 

My thinking is to get financing established through a HELOC so that’s ready to go and I’m not a much of a gambler so I’m not looking to invest in cash flow neutral or negative properties and hoping for appreciation.

One is a gambler, the other isn't.

It's a professional way of saying 'gambler.'

Most over leveraged owners are like addicted gamblers, they don't believe they have a problem (over leveraged) until the market turns and they go broke/bankrupt.

I have always been pretty frugal and think some things are a waste (gambling or designer clothes) but some things are worth the spending (travel)  I was actually in Vegas this past weekend with some friends who were gamblers.  

To siphon the money out of degenerate gamblers' pockets as they curse their luck weakly and yet keep pulling away at the one-armed bandits, oh wow, that's got to be the best feeling ever.