For those owners or folks who are looking to purchase a Vacation Rental, what is the most important part of owning this investment for you? 

We  closed on a 128 unit deal last year, price of 9.6 million, and the owner held $450,000 as part of the down payment.We've also done deals with 80% bank and 20% seller carry back.The cycle has shifted to where seller financing is being used more often.Good LuckGino

If you put up $100,000 and fail to get financing the owner isn't really going to mind keeping your money and calling one of the other two offers up. 

As a result, I discovered that many aircraft owners like me were experiencing a shortage of hangars.

Similar to what @Sarita Scherpereel says, a house hack will mostly be about the equity you make and total return after moving in low down as well as hopefully lower cost of living while you are owner occupying it.

From experience as an owner and a student, I think most would want to bring their own furniture themselves with the exception of appliances like fridge/freezer and washer/drier. 

You give up some liberties when you owner occupy.

My boss owner financed the current home im living in for the past year and half.

I'm unsure what the right path is, but I've been reading about investing in owner-occupied, multi-family properties.

But I have been thinking of maybe sending hand written letters directly to the owner to try to get one under contract.