If you think the state and IRS cannot find your real estate, you are taking a big gamble.

Of course, vagrants could be their replacement if they move... so it's your call and your gamble to take.

It looks like you have done fine so far but you are taking a gamble. 

Is it gambling?  

@Justin Bell - If I'm reading this right, you are using an application that violates Craiglist's policies, to scrape information off Craiglist's site, then spam the same list of people that you captured from Craiglist's site?

Possibility of sports gambling?

I'm of the opinion that there's not a ton of morally black and white issues.Pricing is one of those things that is fluid and needs some feedback to confirm fair market price.I don't stress it - from both my time going out to do research on what places are worth on the front end, I assume that people shopping know that not every place they reach out on is a winner.Granted, there needs to be enough 'real' listings and non spam etc there to make a zillow or other place to advertise worthwhile to draw users.  

In my area distressed properties from wholesalers usually are in distressed areas so the purchase is a gamble on the condition of the property, a gamble on the area than a gamble on hired contractors.

Keep in mind that purchasing a list from a list broker will likely mean they have sold that same list to hundreds of other investors, possibly thousands and those poor people on that list likely get junk mail and spam calls all the time.

A lot of bigger wholesalers or less experienced just spam out a huge list of everything they have and a flipper may ignore their list if they have to look through too many deals.