However, if cash flow is important to you, there are other properties on O'ahu that would make for a better investment and that your family might also enjoy.  

There is risk with any investment, anywhere, but airbnb does well here - if you buy the right place.Locations: this is important.

(I recently saw an article in Forbes talking about the Bay Area’s shifting market) And if you aim to hold properties long term, keep your eyes on towns around the Bay that have had consistent rent growth.Here in my home market of Phoenix, I see investors branching out to places like Austin, Chicago, and even Omaha from what Ive heard because they recognize how trends can shift quickly.

This is very important. 

https://my.aarpfoundation.org/article/renter-eviction-assist...

It is also important to consider the transactional fees associated with originating the HELOC, whether an appraisal is required etc.

Offering flexibility has allowed my borrowers to swing into deals they would not have been able to do previously.You’ve made a great point about the importance of being easy to work with and fostering strong relationships with lenders.

Once you feel you've built a strong team with your first property and have solid systems in place, I would then start buying more aggressively and taking on bigger projects.I suggest reading this BP article on the core 4.https://www.biggerpockets.com/blog/core-four-real-estate-team

Very important detail. 

By 2030, we want to have grown a portfolio of over 100 units, created a property management company that manages an additional 100-200 units, and, finally (and most importantly), we will have established a non-profit that is focused on quality, affordable housing that specializes in providing housing and resources at/on the "services cliff" alongside financial counseling and first-time home buyer education in our target area.Our target area is the Springfield, MA and Hartford, CT areas with dreams to expand to Central Massachusetts (Worcester, MA), Southern New Hampshire (Nashua, NH), and Southern Connecticut (New Haven, CT).Would love to meet up with likeminded individuals in our area!