Short-term rentals can be a great starting point, especially in markets with high tourism or business travel.

Here is some info: SF STR FAQAssuming the info is up-to-date, it must be your permanent residence (you must live at the property for a minimum 275 days a year), you can rent unhosted a max of 90 nights a year, you need a business license, and you need to pay the city $925 for a STR certificate.

"Chasing" after a tenant is not good business and will waste a ton of your time.

That said, I've seen many of these carriers are pulling away from habitation exposures (non-renewing a good portion of that business).  

I am looking to network and build a strong business relationship with a local real estate agent.

This is a business purpose loan and will have a prepayment penalty and possibly cost a bit more than conventional financing.

From what Ive read, it looks like I may have to get a business certificate to do this in SF but Im not sure what that entails or what else is involved?

I don't know how that business could survive long-term with such low rates.If those numbers are accurate and you can net $38,000 a year, then it's worth holding onto.

I was raised in the land business and sold land exclusively for many years.

I have managed STRs for 10 years in Los Angeles, so I understand the business and operations.