Like many, I take it, we'd like to achieve a certain sort of lifestyle that keeps us connected with the people and things that matter most to us.We are also looking forward to meeting some good people in the area, as aside from some cousins of my wife's who live in N.C., we know basically no one.  

Then he can sell if/when he's ready for the $90k (or more, depending on how long he holds it).Wouldn't those two scenarios achieve the same thing?

This would give you first hand experience, and into a property with a smaller downpayment

Not saying it is not achievable. 

Jumping into the pool is the most important step to achieving your ultimate goals in REI.joel

I am thinking should I pay for a real estate coach to help me achieve my goal.

I have goals that I want to achieve.  

Could you achieve a better yield by investing elsewhere in the U.S.?  

We do live in one of the most expensive areas in the country, but there are many of us based out of the Bay that make it work - and you can do.Start going to some of the local BP meet ups and tell everyone what you are trying to achieve and just listen and learn to how others are making it happen here.

For example, if you have a one million dollar portfolio earning you 5% ($50,000/y), and you "borrow" $100,000 of it to buy you a rental investment, then all of a sudden the stock market nose dives so that your portfolio is only valued at $700,000, all of a sudden you owe your portfolio one dollar for every seven, meaning that your portfolio is only worth $600k.But if you had only used $20k and took out a normal mortgage for the other $80k, your portfolio would still be worth $680k.In both scenarios, the value of your property investment will likely have fallen by the same proportion, so the real question becomes: how much built-in equity did you manage to achieve to begin with?