Therefore your overall rate of return spread becomes far less.

Working a 9-5 job with very little return in a 401k and Roth IRA and having to work until I'm dead is not a life I want to lead.

(Self employed general contractor, income low on tax returns, but own house worth $1.2 million, no debt)Would love other opinions on this, not just our realtor’s.

They could certainly search the websites Hawaii rentals and compare next year to tax returns. 

Calculate your return and see which one has a better ROI.

Everytime is a good time to buy if you get a good deal.I would focus in on your goals, and what returns you expect for a deal.THEN look for those deals and buy one if you find it.Yes its getting a lot more difficult, we personally are finding it a LOT harder to find deals we like. 

I'm trying to see what kind of returns I could expect after getting a great deal in an A/B neighborhood. 

Run the numbers and walk a lot of properties prior to as well so you can get a feel of what kind of returns to expect in the different areas.

@Edison Reis,It boils down to if you will earn greater return on investing outside or paying off heloc. 

My wife and I have four multiplexes in Hampton, VA and our returns are in that range.