If the siding is cement based asbestos siding,  going over it with vinyl would likely cause breakage leading to a hazard.  

Hi everyone - Just getting started in the wholesaling business, hoping to start meeting with potential sellers soon. Ladies - do you bring someone with you when you meet with a seller? I can't see myself ever going to...

Can it cover Multiple properties and does it come a lot cheaper than having Landloard Insurance (Covering Fire, hazards, Wind... ) ?

In SF there is a lot to consider given schools, proximity to grocery stores, ease of parking, safety to walk alone at most hours of the day, proximity to restaurants etc.

Especially for E 83th St, how the overall safety in this area?

Roofing contractors I've talked to also do not like wood shake as they state that insurance companies don't like it due to the fire hazard. 

The most important thing is to build in a margin of safety, which is very hard in today's environment.

Go to the local building and safety department and bring the address & APN of the Property.

When making this decision you should factor in a whole lot of other things as well (income, retirement, safety money, etc.) so I am not going to give you advice on that without knowing your situation. 

Thanks @Taylor Hazard and @Bryan Blankenship.