Ask them if they expect housing prices to drop, or just not go up as fast, and then challenge them on their assumptions. 

I think cash on cash return and assumptions can really change ROi, so when i compare projects it's always using 100% cash.

Many/most of your assumptions are incorrect.

Just to rub it in, here's another thing wrong with your assumptions: of the >$50k you'd be paying over the next 2 years (for PITI alone), only about $7.5k would come off the amount you still owe!

I've always operated under the assumption that research is extremely powerful and this makes you prepared to navigate through obstacles or reorient your "path" and be comfortable in doing so.

A lot of assumptions made here...

There are a lot of assumptions I made with expenses/cap ex, but I couldn't get a positive cashflow if you were actually to totally rent both sides out.  

Again, irrelevant in the "real world" but as a thought-exercise you'd just replace one set of value-assumption-arguments with an appraiser for another

Then make sure you buy, renovate, and operate in such a way that you have multiple profitable exit strategies in case any of your projections or assumptions are off.

It's really hard seeing how well people are doing with cashflow properties :(Other assumptions:- I have the funds to buy here in the Bay, although I don't want to gamble on further appreciation, I really like the idea of cash flow- Other than building wealth, another main goal of buying an out of state property would indeed be diversification from the stock market, which is wise in my opinion considering the crazy run of the past 7 years- I am aware there are other passive options such as investing in debt deals via crowdfunded portals, but those to me just seem a meat marketplace, plus you don't recoup any of the advantages that come with leverage, tax efficiency and building equityThanks