San Francisco or Oakland

[Sagar Mata]

Hello there-

I'm looking for some perspective from the forum:

I currently own a SFH in Temescal Oakland and have purchased another SFH also in the Bay Area that will become my primary residence.

My original plan was to rent the Oakland house, but now I'm wondering if it would be a better deal to sell and buy one (or two) condo(s) in San Francisco. My plan is to hold for long term appreciation, but also want some positive cash-flow day one and I think I can easily do that in either Oakland or SF.

Here are a few more details and things I'm considering:

 Oakland:

The house is old (1920s) but in good condition. 

I would not be able to afford a property management company at this time. I'm ok to manage day to day tenant requests but as time goes on, I'm not sure I want to be managing a new roof installation, furnace, etc as those become necessary.

SF:

I understand HOAs can eat a lot into my potential profit, but from what I've seen, the rents are such that they would cover all my costs (small mortgage, HOA and management fees). Cash flow would be bit less than Oakland but I would not have to deal with managing anything (plan would be to buy in a building where management is included in the fees).

Looking for opinions/thoughts on what would be a best deal.

As always, thank you in advance for your time and advice.