For example, managing a luxury building requires a different level of service and communication than managing a multi-family unit.

I decided to look into an official duplex or triplex putting 150K down that has value add with renovations and potential unit add but it wont have as much equity because it will be an on market deal. 

Our laws require us to offer a rental first come first served (first completed application that qualifies must be offered the unit).

But if they gov't changes to a 90 day minimum, you would have to operate as a 90 day rental or longer.And talking to local experts, if you want to own a STR on O'ahu, your safest bet is to buy a unit in a Condotel that is located in the "Resort" zone of Waikiki.  

Like deferred maintenance, (bad roof, worn out water heater/AC Unit, warped flooring, water damage) etc, unpaid utilities,  unpaid taxes, a second loan, unpaid HOA fees, a bad pool, bad reputation, sometimes squatters, sometimes they were drug houses, and so on.

Assuming you have 5 units, each worth 300K, and you could afford the loss of one, but not all.

When I ask for an income report, I received a spreadsheet with multiple units. 

If there are people there will be a need for MTR-- getting your location, unit size and pricing to align is the magic sauce.

Then, how does that look if you were to updated units and move out and rent both sides? 

I plan to live in the multi-family for a year then move out and rent the unit.