Aloha @Daniel Kam - most of Kakaako has a 180 day rental minimum, so if you haven't checked with your building association, I recommend you verify what the minimum rental period is for your building.If you are allowed to rent for less than 180 days, you will then need to apply for a GET license, and well as TAT/OTAT and pay the appropriate taxes on a regular basis.  

I have been all over the world and tour investment markets regularly throughout the US.

Anyway back to regularly scheduled program !!   

Your best bet is probably to get your real estate license and start actively being a real estate professional or buy a STR in your market that you can physically be at on a regular basis. 

On the other hand, true private lenders are not professional lenders and hedge fund type lenders (which is what hard money lenders are), but instead are regular people in your circle and sphere of influence.

Plus you’re moving regularly.

Yet, I regularly correct major errors made on tax returns by HRB people and even by CPAs.

I spoke to several of the insurance agents we use here in the Disney area and they have all said that policies are regularly being written and by all they hear, will continue to do so. 

Most cities have regular real estate meet ups for investors which is often the easiest way to meet local flippers.

Our mortgage brokerage works with real estate investors all across the country who face these same decisions regularly.