I would have hated to see the total cost of that bill.Then in July or August last year we had soul shattering hail.

They offered me a pretty high quote though - $100/month for a $500 deductible (lowest deductible  they offer), that covers all perils including wind, hail, and vandalism.  

A few weeks later a big storm comes through, and now I have a leak in the roof of my rental after a few shingles were blown off and heavy rains and hail slammed the area.  

@Ken Teng CA insurance premiums are low compared to Midwestern states that have frequent Wind/Hail claims.

We are currently having to replace a roof, due to hail damage (not uncommon).

I would not personally buy where the front of the house was to a very busy street, where kids could get killed in traffic and you have to say a hail marry before exiting the driveway directly onto the busy street, but backing or siding to a busy street if priced properly and with other redeeming features has worked out well.

So, I thought I would throw a hail mary and see if anyone may be able to use my skills.

He found we had some hail damage from a storm back in April and State Farm has agreed to replace two sides of the aluminum siding.

This is important at claim time, think about one hail or wind storm doing damage to multiple units, and now you have to manage a different claims adjuster for each property.

A short sale is a Hail Mary at best at this point as:-The OP doesn't even know if there is any equity- The owner may have assets and therefore to pay so no reason to do a short sale- The POA issue.