With the switch to more remote working and schooling, it seemed like a good gamble. 

and refunds to guests2) Hire amazing people - cleaners, handyman, recruit some neighbors to help fill in the gaps, & self-manage or hire an offshore VA to manage the property if you'd rather make yourself rich instead of making a local property manager rich (more on that here: https://www.biggerpockets.com/... )And make sure that your cleaners and handyman are not only doing a top-notch job of keeping the house in pristine condition, but they are also reporting to you (or to your PM or to your offshore asst) every little thing that needs to be upgraded or replaced so that you can stay on top of it and take care of things before you hear it from your guests in the form of guest complaints and bad reviews.

Am I doing risky gamble here? 

Pretty good gambling opportunity for a smaller outfit.

Like Vegas has, AC needs to be entertainment first (with that little taste of sin city) and gambling second. 

It's bold, but sometimes bold gambles pay off big.

Trying to bank on appreciation is gambling.

In the case of PA it's first come first serve, so today being the deadline to apply, it's also a gamble whether I will even get $750.

Everything in this game is a gamble, but most times, it all works out in the end!

Horrible offshore customer service.