But if you're going to use all cash and therefore gamble large sums of money at least promise me you won't try to juggle family, a flip, and a full time job.

No one can answer if interest rates will go up or down in the next 2 years, but if you had to gamble you'd gamble up since they're already near historical lows. 

Just my opinion but it is safer than gambling in stocks, I call it gambling because I do not have the time nor the drive to learn anything about them.

., where it was previously headquartered.High-pressure sales tactics were used to secure money for what were promised to be “low risk” and “conservative” investments, but in reality the funds were funneled to real estate owned by Shapiro, according to the U.S. attorney’s office.Woodbridge eventually became financially insolvent, the scheme began to unravel, and Shapiro in 2017 considering filing for bankruptcy, prosecutors said.Still, he, Roseman and Acevedo continued to sell the fraudulent investments without telling investors Woodbridge was on the verge of collapse, according to the indictment.

Unless the deal that you are getting is worth it the gamble. 

However, I am not 100 percent sure this would be consistent income so it's kind of a gamble.

Should I wait and gamble that they won’t sell so I can do a conventional loan to buy both? 

I see it as more of a gamble than an investment.  

Should you decide to gamble on your crystal ball and you manage to achieve 100% occupancy with an average rent of $735 a unit, that puts your GRI @ $52,920.

Home warranties are just like gambling...