The only things different about Section 8 are they have an additional income line (assistance) and some additional regulations on the property as a result of the Section 8 lease and inspections.  

Depending on that, I might consider a couple of options. 1) bring the rent to market but suggest to the tenant that you would consider rolling back after the outcome of the Prop 10 vote. 2) Just do the 5% if you think that although the City of Oakland will have the power to implement vacancy control, they may take time to decide how to change any existing rent control system in place.Bear in mind, I am just thinking out loud...I do not know Oakland but also am thinking there may be opportunities for buyers being created because of this Prop 10 uncertainty. 

When rent increases are regulated, the profit source from rent appreciation is capped. 

I noticed the Alerts feature, which I believe notifies you of new posts with specific keywords... but is it possible to search existing posts using specific keywords?

First deal...I'm interested in a duplex where the bottom unit is rented month to month. If I purchase the property, Im planning on running his info doing a credit and background check before signing a 12 month lease. ...

Only that in my honest opinion, what you're asking for on the realtor side doesn't really exist.

My question is, do I not have her sign my lease until her current lease expires, or do we use a combination of both the existing and new leases?

There are no heirs to the best of my knowledge and there appears to have been a falling out among the late owner and existing relatives.

Many banks will shut down accounts if/when they realize you're accepting payments from a dispensary because it isn't legalized at a federal level, and banks adhere to federal regulations.

Feel like the existing retail there has a good feature that will keep them going for many years.