I’ve also built a website with a ton of resources on investing in the area, like market insights, networking opportunities, and local expert connections.

If you cannot clearly articulate why these are strategic locations that will reposition themselves and the guaranteed rent is the only way to secure paying tenants then you are operating a business, not investing in real estate.  

Most were in risky neighborhoods, but did offer security provided by the corner drug dealers.

It is essential that you consult with an experienced cross-border team including attorney(s) and tax expert(s) to ensure that you access the right advice!

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?

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.