Plan is so that he can retire and him and my Mom can be financially secure on rental income while my sister and I manage the properties in the trust. 

How are landlords in SF handling the security deposit law that requires them to pay interest to residents on their deposits?

Keep in mind you need so many different website plug-ins and features and you have to make it secure for credit card processing.

Also, what about internet, trash and security?

When I say fire fast - do not get emotionally attached to the contractors.

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.

The short version is this:  If you're willing to pay (considerably) more for the security of guaranteed rent, they are probably worth hiring.

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.

My tenant of 1 year just moved out recently (work transfer), but during the move-out inspection we found that one of the 10X10 bedroom has all four side of the wall covered in screw holes from the time they used it as a computer room (I believe the holes were from the sound deadening foam that they used to attach to the wall) So I was wondering what would seem to be a fairly reasonable cost to be deducted from their Security Deposit for the excessive holes and needing to repaint.