With the stock market literally about to do a huge correction pre election I think there will be quite a bit of money to be made on shorts.

Is your $2k per month on $600k equity correct?  

However, I know that I do not want all my income to be reliant on my day job and live to watch my retirement account grow.I am probably doing better than a lot of people my age but am eager to take the correct steps to build a real estate portfolio.

I would confirm the other four owners and would not buy there is they were all the same family, it will just be miserable most likely trying to deal with 4 against 1 (unless they all hate each other).Your second concern is valid and correct.

But, you get the piece of mind knowing it’s likely done correctly.

So saying people can’t do the rehab or don’t have the money is not entirely correct.

It does feel like there is likely a major market correction coming, but due to limited inventory of vacation-rentable units in Maui I feel like I should be somewhat more protected from the effects of said recession.

@Dennis Boettjer - everyone's comments above are correct. 

You may want to think about working with a realtor or a really good attorney to make sure you are set up correctly to start off in the best possible situation. 

You are probably correct.