Look You can’t live your life in speculation mode pondering the world markets with the covers over your head .

I am beginning to speculate that the reason for him selling might be mismanagement (I have several reasons to believe this, my realtor also is starting to lean that way as the seller has just said he wants to be done with it). 

This is unlikely to work because it's highly risky, and nearly speculative for the bank.

He sounds more like a speculator than an investor.

Yes, it's speculated that factions of Al-Quida were the culprits.

To me It doesn't feel the same as say, buying a house in 2006 and speculating that the price will continue to rise 20 percent a year.

These were speculative plays.

It was a sight to see a good learning experience. but this was in 2006 he speculated and lost like others during the crash.

Don't speculate on growth. 

There isn't any consistency in evaluating ARV, so flipping would be more speculation than investing.