It would be a big gamble to buy this thing and not break even and then enter into any sort of issues with maintenance or finances.

It might have enough appreciation to offset all the money you throw at the house in payments and maintenance, taxes, etc, but if you want to gamble with your money, there's better ways to do it.I think you need to start with goals and decide if this deal lives up to your deal standards.

Have you ever gambled any game in casino when you were in Vegas?

We're not talking SF-over-the-last-10-years appreciation, but I'm interested in predictable investment returns, not gambling.

You do not want the neighbor listing on mls or other network because you have no way of knowing what someone else will pay for the place (of course, it could also work in your favor but that too is a gamble).

I can gamble and wait till I sell my flip but not sure if the timing is going to be right.  

I think speculating on amazon would be a huge gamble at this point.

Is he a doctor from the UK who's moving to the US with his daughter?

If you, based on market indicators, believe that there will be appreciation then hold on however we all know that's a gambling mans game. 

Deja vu from 2005-2007..........Yes, you need to leverage your equity to keep moving forward....wont argue that....but to pull out ALL your equity to go buy more properties in a very high market, sounds like a huge gamble to me..... use the leverage....hell yes.....but using ALL of your equity is a huge ALL IN bet..... you better be able to back it up if there is a big correction......Guess I'm just a wimp.....hope you are right.......