Without payoff and lien info, this is a complete gamble for you, IMO.

People getting CC numbers from dark web and booking through our site or another platform. 

At the moment it looks more like gambling.

It's all relatively available, readily available on the web. , so if you like digging down into that data, start with city data and census data and you'll get some good data, to evaluate those markets. , so what's what's the conclusion, , is there a best market to invest in?

Gains through crypto felt uncertain to me but still had a draw, so I decided I wouldn't use more than 5% of my disposable income to gamble (whether on leveraged index funds like QLD or crypto).

Web based management software and smart phones shortened the lifespan of kiosks! 

Is it a gamble to move into one of these neighborhoods if the market crashes?

@Flavia Vangelotti forecasting appreciation is always a gamble so I view it as a bonus on my investment properties. 

So ah, Whats Bills web-site?

I have a modest background in web development and have been rebuilding a separate direct-booking site to align with a broader pivot to off-platform direct booking.