If he gets a judgement against him for any reason, a lien could and most likely would be attached to 'your' property.There is also legacy risk. 

These are big players though with lot's of money and properties.An investor with less experience there can be more risk in leveraging especially with limited assets as a mistake can be greatly amplified.

Too high a risk for too low a return. 

If people cannot get in the risk of buying goes up exponentially. 

I am curious about any differences in management, expenses, risks, etc..

You will have negative cash flow and will only be able to rely on appreciation to profit....extremely risky.Additionally if plan A is a serious option for you then you are a very low risk investor and may want to reconsider directly investing in real estate and may be better off putting your money in a REIT.A investor, assuming they have the ability to move, would sell the CA property and move their money to where it can actually produce positive cash flow.

The professional who knows who they're doing for $100/hour or Bubba down the road who does it in his spare time for $15/hour, carries no liability insurance, and will not be there to make things right when your engine blows up?

How can we go about taking a CALCULATED risk?

Whatever the outcome, he should not lose his will and desire to own, manage, rehab, leverage, take risks or be a student of real estate investment.

Anything else has a risk factor of turning off some buyers.