I think this is a good start but ultimately from a neighbor's perspective in a residential neighborhood I think an STR next door has to be a net positive and not just neutral.  

In either case if you buy one that needs a little work you should be able to create some quick equity. 

You know we can eventually figure out the Lawbreakers that come across as Clear.But I wonder how many "Clears" come across as lawbreakers (False Negative), because that seems as reasonable as a (False Positive).

Immediate positive cash flow How did you find this deal and how did you negotiate it?

I am moving to Oahu with my girlfriend and we want to take this opportunity to transition from renters to homeowners and from consumers to investors where through house hacking we would end each month cashflow positive.

He has a ton of equity in another rental so they suggested to do a cash out refi to buy another (sounds familiar). 

You have money - in the equity of your property.

The 80% LTV should be fine, I have plenty of equity in my property.Thanks again,Hillary

The properties are high equity single family homes in A to B area(s). 

Currently I have a traditional IRA in my Fidelity account sitting in cash that I would like to use to invest in a cre syndication or maybe a note or debt fund... but first I would need transfer funds into a self directed IRA with a company like Equity Trust.