I like my investors to keep their investment, not gamble it all away. ;-)

Take calculated risks based on your own risk tolerance, don't make decisions on a gamble or without verifying it for yourself, and don't pretend to know what you're doing if you have no idea what you're doing.

She had built up a buyers list of real buyers over the years, and was willing to gamble with relatively small option fees when a seller was willing to price correctly.Now, it can be argued that she should, or at least could acquire a brokers license.

It's a little bit of a gamble though and why take the risk if you don't have to.  

When the balloon payment comes due, you just need to "pay the piper" and see if your gamble paid off.Does this help? 

But for now, I'm letting the "gambling" money ride on black.

Looking for a "sanity check" from the expert community.

Wife and I purchased a home in 2005 for $360k with one of those wonderful 80/20 interest only heloc deals and I am paying about $1300 per month (3.25%) plus tax...

The best developers don't gamble.

I decided that the only explanation is the smaller guy bid and he hoped/gambled I just got one bid, and the winning bid had sunk costs in trucks and crew so it is more about getting every job they bid and making more on guaranteed volume vs fewer jobs but higher net per job. 

I would not take it lightly either .. this is almost setting up for an episode of American greed  :)   is this the episode where we learn he gambled away all the security deposit and used them for lavish trips and lingerie for his wife?