"Pure speculation" you say, and only need to point back to the early 2000's to see where that type of investing got us.But here's the thing... real estate cycles go up and down.

Little things like that were what made pre 2016 version great I can speculate.

I'd speculate after the 100-day mark they've probably received multiple offers that were also below ask and the realtor knew their client wouldn't be interested.

New construction in the commercial real is a very speculative affair and is a very advanced concept.

But they are consistently hitting 15-25% returns.Then you move to the second tier of sponsors where the deals are more speculative (think Vegas land plays ten years ago) or the deals are relatively small (e.g. inner block development).  

I am not a speculator by any means, and find it too risky to bet on short term appreciation.

...I'm going to speculate a bit here, but my guess is that MOST FSBOs aren't on the MLS.

Speculating on appreciation?

Like many wealthy people, he may have done it simply to have one part of his nest-egg be worry-free and the other part be more speculative.

If you aren't hedging you are speculating and all investments bear risk.