@Caplan Abbey where is maintenance, repairs, less vacancy, ground keeping, service repair (pest control, hvac), water/sewer, management fee, advertising, etc..

You can't control your schedule and you could come up for TDY or a deployment with no notice.

Your cash reserves are not a cost to you...that's still your money, and you still have 100% control over it. 

real estate is anything but no work  yes limited to no physical work but to be able to live off of your investments takes time and frankly more seed capital. but the biggest bang for your buck with 100k is going to be using it as a downpayment and do fix and flip... but you need to be very cautious.depending on your market this could be one or two flips that would make 20 to 30k each and you could do two a year.not sure if 40 to 60k a year income would do it for you.. some it will some it wont.. rentals NO way no how not in todays markets..at least to start.you could do the BRRR pay cash and refi.. but yoiu need a job and great income to refi.. ?

The trust owns the property and is controlled by the trustee.

While some people are making it work it’s illegal in much of the valley and limited to 1 every 600’ in the rest and/or a minimum 30 day rental.

I found with real estate I had more control, and higher & more consistent gains so I focus on that.

Are you planning to flip or buy and hold, from my limited understanding Auckland can be rough for the latter. 

I just want to automate routine AirBnb message traffic so I can limit the amount of time that I'm on my phone during the day while still keep customers happy (VRBO / Homeaway don't seem to need instant responses in my area).  

My knowledge of them is limited so I can't speak to their business model.