We have two tenants who never pay due to their pay day schedules (and of course living paycheck to paycheck).  

As Jay suggested, if you think you are buying a good deal, be careful some of these areas that are being sold to people from California, Washington, Hawaii, New York, New Jersey, and even Texas now are being led to believe they are buying "C" class and "B" class properties here on BP and they are really scary "D" class properties.Make sure you google earth 1/2 block away to 6 block radius at all the commercial, shopping etc... if you see grafitti, broken windows, boarded up windows, trash all over the place, payday loans, unsavory characters, NO large grocery stores, NO trendy shopping, coffee shops etc...  

BRRR also works and deliver a great pay day if you are able to maneuver through RSO and building codes.

The correct answer is then to rework (Airbnb) or sell this money losing business and move on.But no, everyone has instead convinced him that he is a brilliant “investor for appreciation” and he is going to hit a million dollar pay day! 

Not bad a bad payday but I’d like to keep mine as a long term rental.

First, from your telling of the story, these tenants are trying for an unearned payday. 

I’m literally stretching my last dollar till next payday.

I got a nice payday when partners bought me out.I just wanted to focus on ( like you said on two basic business models that I enjoy far more than SFR middle America rentals).It will be intereting to see how your portfolio is doing at year 5.. that tends to be the year when you have full cycles on most.And I am thinking Omaha may not have some of the issues some of the other mid west cities have vis a vi tenant base crime etc.I worked with a company that did IRA set ups for a time. and their story was the same as yours with google. for years they were killing it then google changed pricing and what was a few grand a month was now 50 to 100k a month.

Had he done a minimum of work, this would have been a nice payday for him.My primary agent goes with me to a property and points out every subtle defect. 

I really think she's trying to set me up for something that gets her a big payday.