Current tenant has been there 2 years, is now a single mom and has a good job as a nurse, but is constantly late on rent. 

I don't know about the specific add ons you listed, but I do know that my insurance went down when I switched from a homeowner to landlord policy on my single family homes. 

That said, although I think it's one of the hottest parts of San Diego, I still would be wary as a single woman living in parts of Sherman/Grant Hill/Bario. 

If single family home do a survey and check for boundary violations etc.Unless you are getting a sizable discount this may not be worth the effort.

@Jackson SandlandI don’t imagine a single business would have a real effect on property prices .

Most of the cities and towns you listed are mostly filled with single families, though.

I am focused on a buy and hold strategy with single family or small multifamily homes.

In house hacking, I believe the idea is to buy a property (single family or up to 4 units) using a conventional fixed rate loan with a low down payment and then to live in it for the required time and move on to buy another property the using the same method.

After that year, we had two rental properties that each cashflowed $200 per month and we didn’t have a single dime of our own money invested.

I am in Philly working on a single family buy and hold.