Reality: still here, only a temporary increase in the exemption.- Plan: eliminate NIIT - Net Investment Income Tax.

But, you will have increased the value of the property, allowing you to pull cash out for your next deal.

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?

As far as the tenant goes, it sucks to have to raise rent but its still a business and its likely that if they try to find another place, they will be stuck paying even higher rents than what yours is at if you increase it to 90% of market value. 

@Ashish Acharya A big part of my post is highlighting how specific details in local regulations can make it increasingly challenging to operate short-term rentals, even in towns where they’re technically permitted.

During turnovers they fix everything, and by everything, I mean they look for anything that they can do to increase the SOW in order to skim as much as they can off the work costs.

Utah has some of the cheapest tax and insurance rates, but their rent to price ratio is horrible and rents don't keep up with housing increases like they do here. 

I once rented a 5bed/3bath in two days, just a week before Christmas when the ground was covered with snow and ice.Sitting vacant in the winter increases the risk of frozen pipes or other expensive problems.

Increase time spent conversing with each lead that you get to learn more about how they view the property and implement reasonable changes accordingly.

You will get away from income taxes and annual registration fees by going to the townships, but your property taxes skyrocket which may offset some of the rent increases.