The indicators given were a historically high amount of equity in primary residences, employers using bonuses to reward employees vs. salary increases, and college students choosing STEM degrees vs. liberal arts degrees. 

I could get about $300 a month positive cash flow, and I own the property free and clear in 17 years.So I guess the real question is, besides rare circumstances like this - what would be a reasonable reward, payment, etc. to make it beneficial for me to dig someone out of a hole and make it worth their while to trust me for the next 15 years.

Don't be afraid, and have the courage to learn something new and if you put in the effort I'm sure you will reap the rewards.

Account Closed Oahu can be a difficult market to break in to, but it can also be very rewarding. 

Everyone shares the risks and rewards and you don't have to go into a deal alone.

Happy to share more details for those interested in my situation or want to charitably help me make some critical decisions in the next couple days.Here is Brian's article I'm referring to: https://www.biggerpockets.com/renewsblog/2013/01/2...

Pardon my memory, one of the interviewees in 2016 made a statement I really liked for this conversation stating that while he quadrupled his investment since after the recession- he didn’t see his investment quadrupling again. it’s risk/reward.

This will be the first project for my group and myself so the whole process is a bit challenging but, rewarding in the long term.  

Those are roughly in risk/reward order from lowest to highest, though they will all give you some hedge against inflation. 

Put pen to paper, see if the cash flow, appreciation, risk, reward all work for you or don't work for you.