Although I wasn’t entirely thrilled by my last 1031 exchange due to not securing my replacement of choice. 

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.

I am a newbie to the REI world and I am thrill to be here.

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? 

Don't expect the seller or listing agent to be thrilled if you request repairs when you agree the property is sold "as is".