I broke down the costs, and designed a whole new home thinking of all of the connections that I have through out, crunching numbers and trying to determine risk versus reward. 

I'm essentially looking at the rents in the area versus my expense analysis on the property and trying to find deals that the rent surpasses that expense theoretically.

You will end up paying more in closing costs this way because some costs will be doubled, such as recording fees and title insurance.Many lenders require 6-12 months seasoning and charge a slightly higher interest rate for cash out refi mortgage versus purchase mortgages.  

Thanks @Sean Davidson @Roger Poulin @Bryan WallacePer Roger's suggestion, I researched the FEMA map versus the topography.

My Ranges will cost only about $500 brand new (I just bought a new one today).I don't think the one shoe fits all works for $100k multi-family buildings in low income areas versus high Multi-Million Dollar multi-family buildings in dense and desirable areas where you can command high income.The two kinds of investments need different calculations and strategies.I absolutely know these differences because of my other friends that decided to invest in non-Major Metro areas outside of my Area.

I am in the process of trying to establish something similar to Joshua but something where its a longer term stay versus a couple weeks or so at a time (different area of the US). 

So if you find something wrong with a property, then don't buy it, and no money lost.I do recommend you work with an impartial advisor versus a turnkey seller themselves.

So that cost has to weighed against buying one home, versus a multi unit.

The numbers don't have to be exact yet.And while you are studying and learning, talk with a couple of loan officers and see what type of products they offer and what it looks like to have a commercial loan versus residential.

Buy from Profit and Loss statement, not emotion.If buying to hold either as long term vs vacation rental do the math of Initial investment versus return.Cost of return vs Investment cost may be more attractive on Maui