My wife and I just closed on a duplex in Oakland, but the basement/garage was already converted into a separate living space with a bedroom and bathroom.

If you have other money besides the 20K then this is a different story Already living in a house I bought before Covid.

Because if you need to live off the cash flow what you're really looking for is a business. 

It is live and able to be edited or changed anytime.

Is it an automated voice attendant, is it a call center where you are routed to someone else eventually to get an answer, or is it a live, well trained staff member?

You'll likely also reduce your cost of living by moving to a stabilized apartment.Depending on the cashflow and debt paydown, you can use this strategy until you've built enough equity to reinvest.On the other hand, getting into a multi-family after refinancing will also help you build substantial equity to rinse and repeat in the coming years.

It very well could become a large enough investment to be worthwhile, also solving for "unexpected emergencies ", for the most part and would an easy self management situation if you were to live onsite in one of your connected townhomes.

Have enough that after you buy the property you still have 6 months of expenses in reserves that you can use for daily living.

P.S; We live in Wilmington NC so both markets would be "long distance" P.S.P.S there are no reasonably priced multi family properties local to us.

Even though we live in earthquake country, this was a new experience for us.