And being in California, you really should be using licensed companies for everything.

The outcome was great.. they secured a mid-century home with a rental unit that offered both a comfortable living space and a reliable income stream.On a personal note, a friend of mine made a bold move and purchased in a slightly less popular area.

If you don't plan on paying cash and have to leverage with an owner-occupied loan product then you should set up your LLC as a property management company because you will not be able to borrow in the name of the LLC.  

We are considering becoming a private lender with them and I am doing some background research on him and his companies and wondering if anyone has done any deals with them.

A professional trustee such as Exeter Trust Company is the way to go if you want it done right, imo. 

But with the EOY right around the corner need something more reliable. 

Specifically, is the rental market stable, and is reliable assistance (like agents, property managers, contractors, etc.) available?

Plumbing company says its the only way to resolve the issue I have.

The specialist I recommend you have is an attorney to properly draft the documents and a title company to facilitate the deal.

I wasn't sure how much to expect from the title company in resolving this.