My theory is that since there is such massive insecurity in not owning the roof over their heads, surrounding and in some cases burying themselves in junk is like self-medicating against the anxiety.

Those properties could could sustain a massive hit to value and still deliver him a big chunk of gain simply by holding. 

He had a few other properties in Cancun, a lot in a development community right on the beach, and a pair of massive farms where he had big plans.

If I were to even consider going the multi-family route, I would have at least one business partner (who I'm actively talking about this with).With that said, considering the massive price jumps (SFH vs MF), the SFH is the no brainer unless I'm missing something.

Unless this job includes a ton of transitions, needs massive floor leveling, or has a million tiny corners he'll have to custom cut, then $1900 is pretty darn high. 

Thank you for your response  I think if you listened to the podcast I think you listened to, Grant says later in the episode he has massive amounts of money he sets aside for reserves.

Yup and the massive amount of private capital chasing flippers .. and driving down the pricing..

I have seen some investors with the list in an excel spreadsheet but I’m open to any and all recommendations on how to attack this massive list.

Those paper returns don't always materialize and the property can be a massive headache.

And during the crash Portland is better than most desert areas because you don't have massive inventoryand massive amounts of construction workers like those areas.. that's why the desert gets hammered new construction slows way down and half your work force leaves and there goes your renters..