You really do never know who is living next door...or driving down the street after having a fight with their wife, or....well you get the point. 

From my own personal experience and from others I think most reach the "tipping point" from self managing to using a PM somewhere between 5-15  units, especially if you have a W2 and want to continue to scale. 

They will continue to get 360 month loans for the 'cash flow'.

I hope my entry into real estate will continue this trend.

And you are continuing to invest in real estate a 1031 is a good option to explore. 

So talk to your bank and insurer before continuing. 

Living somewhere that you hate will make for a miserable real estate journey and you'll not want to continue.

Assuming the Oakland rental market continues to remain stagnant/competitive with newer buildings going up, is property appreciation the only way to increasing wealth with my building?

Reese's "free" course is really "first lesson free", then you are directed to a paywall to continue.  

i would:-get the highest paying W2 job you can-save up enough to buy a house hack-house hackwhile you continue to learn and consider the other possibilities you mentioned.