Our long term goal is to build this business to where we can quit our jobs and live on our cash flow, so its a no brainer to me but she is hesitant to put all her eggs in one basket.  

@Ericka Grant - an index fund is simply a mutual fund that holds a basket of stocks that mimic an underlying index - like the Dow 30, s&p 500 (500 largest market cap stocks), Russell 5000 etc.   

Newbies tend to focus on low hanging fruit but savvy real estate agents can point them to overlooked properties that produce.

I personally don't want to put all my eggs in 1 basket (market)...

Dozens of offers with institutional type sellers is not going to bear any fruit.

It made people believe that real state investment is so easy and achieving financial freedom is a “low hanging fruit” which could happen over night.

Both of those options puts you in a better situation financially and leverage wise than total cash injection into one rental.Kind of like the saying "Do not keep all your eggs in one basket" is one way to think about the risk/reward.

There's another deal around the corner.However, this is why I am very adamant about not putting all of your eggs into one basket.

Wholesaling or rental arbitrage may be good fits for your situation, but both take a lot of time, dedication, and perseverance to bare fruit.

Anyone with all their eggs in the Honolulu basket is feeling the pain now.The areas that you mention may not change for another 100 years but you just can't know for sure.