The cost allocated overhead is divided based on number of units across multiple properties and added in.

NOBODY doubts that you are clearing $800-to $1,000 per month and I will say that having been to Hawaii multiple times I know it is much prettier to live there then probably anywhere in the U.S.....and that includes the SF Bay Area where i live now. 

One of the strategies our clients use when they don't need the income right away and are in a position to buy multiple properties is to use alllll the cash flow to pay off each loan in turn, resulting in free and clear properties much more quickly and less total interest paid.

I'm very early on, NOT actually engaged in searching for the a building today.My COH will be $500-800K, I want to be totally involved with every aspect of the transaction, the ownership.I will create a high-quality place to live, a destination to be desired.In your opinion:What are the questions I should be asking?

Hey Troy,If you don't want the hassle of multiple properties, I would sell your current properties to purchase a 20+ unit building.

Most are getting multiple bids at listing. 

Is it the multiple kitchens, or perhaps multiple entrances?

Again, this question has multiple parts and this is a short, rough answer.  

I truly will never know but we got the places both times in multiple offer situations.

I sold a house in December in 37208 and I had multiple cash offers in several days.