He waits months to "get back to you" and he's afraid to soil his relationship with the county?????

I would wait till you have 5% to put down on the new place and keep both as rentals without doing anything to them.

Maybe appreciation could make up for it like Jacob mentioned?

Not to mention you will be sharing the profit with those you care about.

I didn't ask any help from the CPA yet although mentioned it to the CPA. 

First, as I previously mentioned, if a tenant stays beyond the expiration of the lease, and the landlord accepts the next month’s rent, the tenant then is assumed to be renting under a month-to-month agreement.

PT mentioned to that he/she is currently going through a divorce that has not been finalized.

You mention you rent rooms to family which is a plus but do you claim the rents. 

And Oakland is really affordable to all the other Bay Area's mentioned.

@Anthony DelVecchio I would suggest having some amount of money saved in reserves for just the type of emergency repairs you have mentioned before buying your first house/property.