Aloha @Daniel Kam - most of Kakaako has a 180 day rental minimum, so if you haven't checked with your building association, I recommend you verify what the minimum rental period is for your building.If you are allowed to rent for less than 180 days, you will then need to apply for a GET license, and well as TAT/OTAT and pay the appropriate taxes on a regular basis.  

Most importantly, learn how to manage it well so you don't squander your investment.

I had a guest cancel as well and my cleaner refunded the fee from their invoice no problem.

Well no kidding!

I know investing with family can possibly hurt relationships if things don't go well, so I don't want to make any big mistakes since this is a large amount of my parents inheritance. 

My education background is in computer science, mathematics and some corporate finance, as well as have some internship experience in the quantitative finance space.

I know for sure that in my area of Texas (well outside of major metro areas), we've seen the cost to build new homes almost double in price. 

The companies that market themselves as "garage door companies" (residential) also almost always do commercial stuff as well, such as what you are looking at.

The property was my primary residence for a decade and now functions as rental unit so I am happy with the purchase overall and it has worked out well.

There's lots of properties for sale in the Smoky mountains so you may also have a larger selection of options to purchase as well.