I decided to gamble on appreciation and overbid on a duplex that will have good cash flow in Oak Park after losing another all cash deal (I bid all cash, over asking and was outbid by a buyer with similar terms with an offer “well above” mine on a different property in the same neighborhood. 

Offshore is fine, as long as there are some recommendations. 

I have also an offshore entity for some international investments but Anderson is not involved in any offshore structure.

If you're counting on appreciation, then you're gambling - doesn't matter where we're at in a Real Estate cycle.

For that reason I Only use Airbnb and Vrbo so that I can have my offshore assistants screen every guest

They were gambling that the yield curve wouldn’t invert like it did, but then it did, and hard. 

thats the bay area.. .. will your prop do that who knows.. but its only a short term gamble so you gamble 3 to 10k over a few years and see what happens.

A real simple answer, HOUSING is a GAMBLE - believe it or NOT, the Invisible STROKE of luck is at its full force when you buy:Example: hundreds of folks became millionaires who bought between 2011-2013 - TIMING - a stroke of luck - which a few calculated/researched/predicted and hence capitalized on it.There are many types of landlords - frugal/slum-lords/penny-pinchers/businessmen etc. = pick your choice!

OK would you gamble your money knowing there is a less than 1% chance of winning?

I literally felt like I was gambling in the stock market no matter how much I studied it.