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?

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

He had a tech job and we talked the business and he was legit and when meeting the family, they were very respectful. 

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.

We live in California at the moment and I have W2 job and my wife a small online business.

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

It’s a tax office, so I suspect they might be waiting to see how their business performs and the impact of technology before deciding.Thanks in advance for any advice or insights you can offer!

Renting, like hiring an employee, taking on a business partner or client and marring (even more so), are relationships that can be costly if made hastily or imprudently.Like others, I have check lists that I do not deviate from. 

Ive never used a call to action or asked for business here.