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

the market is unforgiving right now, and if you buy a random property by looking on Zillow and turn it over to people you don't know to manage, you'll lose money.with respect to your specific question, if the property is safe, clean, and priced correctly, it will rent. but that doesn't mean you'll make money on it. 

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.

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.

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.

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

You are correct.. don't educate when you lack ETHOS (trust/credibility). 

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

You are probably correct.

@Josie Sandoval, correct, this is very common.