Howdy @Dan GongoraThe closest thing to "insurance" would be a Home Warranty Service.  

While this warranty does not require you to supply a perfect dwelling, it does require you to provide a property that is in a livable condition.

Instead of paying the 1k/mo I pay now, I'll be paying just a few hundred in utilities for my side and to supplement cap ex/repairs.

Still a ways out from retirement, but my goal is to have rental income supplement (maybe eventually replace) the income from my job.

Its a little more expensive but I believe this has a better warranty.

Do you have a warranty on the property?

As a supplement to the good info Nicole left1) You don't need to register a DBA with the secretary of state if you're operating in your own name.2) If you have a regular job and Ok credit you may qualify for conventional credit.  

These have a 25 year warranty.  

I used the $500 dollars to pay for a home warranty plan for the year.

Does a general warranty deed show how much you paid for the property of not then what does