We can't approach this Demographic with a cookie cutter Real Estate solution but rather customize a solution for first time home buyers with lease option, house hacking, and building micro/tiny homes etc..

He also runs a trucking company with multiple drivers and rigs owned free and clear. 

RE for the most part is not rigged.  

Included are oil company executives and bank presidents as well as burly oil- rig workers and busboys.New housing starts also remain low, reaching 7,000 this year through July compared to 38,000 annually during the late 1970s.Meanwhile, property foreclosures are averaging 2,000 a month, and bankruptcies soared to more 15,221 petitions filed in the U.S.

Buy a wall paper cutter and make small circles (the more cuts the easier).  

That I because they rigged everything over the years and want the buyer to be the sucker that overpays and inherits a ton of repairs that will kill returns for years.What kind of money were you putting down??

These would not be cookie cutter lots.

If properties meets my requirements then buy and continue cookie cutter kind of approach so the business can scale.Now after reading last few posts as suggested by @McKellar Newsom and @Chris Clothier and others, I have to add due diligence as one of the important step whether I buy through turn-key or directly from an agent.ThanksKumar

There are many RE cookie cutter attorney's out there that don't understand creative real estate deals.

I was working on an oil rig and bought my dads house that he had moved out of that was going into foreclosure.