I haven't tried kitt.io personally but it appears to provide the service you need.

He makes good $, it just appears as if “something” always comes up... my question is.. if he doesn’t come up with all the money, do I just file for possession and be done with him or give him one more chance?

And you'll want some cash reserves (especially when you get a new property) for improvements and repairs that will undoubtedly appear. 

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And it would be appear on his legal record.

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In the spirit of collaboration, I submit for your feedback my emerging investment plan:Markets considered, favored:Favored: Minneapolis - Strong employment, population and rent growth, in addition to what appears to be relatively low and falling values makes this very compelling.

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It would take less than 10 hours to file in Small Claims, appear in Small Claims, get the judgment, and then turn them over for collections.

Homes still can get sold in one weekend with multiple offers but any rental property that has a flaw or pricing will be skipped as there appears to be enough floating on the market.