NOOB IN HAWAII: Equity vs Cashflow??

[Clifton Monte]

I'm in the Army and we've always been renters, so we decided that our next move would mark the beginning of our goal to collect properties to live in prior to renting out.  Well, leave it to Uncle Sam to start our real estate journey in the ever affordable State of Hawaii!  I'm well aware that cash flow in Hawaii is relatively negligible to equity so I wasn't too jaded when, after analyzing over 25 properties with the Rental Property calculator tool, I only found 2 that cash flowed within 5 years.  I've done enough research to know that although Cashflow Is King, equity builds wealth and can be worth an acceptable deficit in cashflow. 

Here are my questions:

1) What are some rules of thumb to follow when balancing the equity/cashflow dichotomy?

2) What is the difference between projecting PV increases, and speculation?

3) What is a minimum acceptable % of equity gain within a 3 year period in Hawaii?