@Scott Hibbert,
Welcome out to Oakland!! One of my favorite cities in the USA :)
Congrats on keeping and renting out your SFR in Boulder with positive cash flow. I said when I started that I would never sell a property, and so far have not (knock on wood.) I own and operate around the Bay Area, and lived on the Eastlake side of Lake Merritt for a while.
RENTAL
I have some furnished rentals near Lake Merritt and elsewhere in Oakland, but wouldn't be able to quite get to your price point. (these are all private (not shared) places.) But Craigslist is the #1 place for sure. Look for shared housing. Good for you for keeping your rent low for the area and saving your cash.
RENTAL TERMS
I respectfully disagree with @Robert Marston on his security deposit statement:
"It is my understanding that you will pay first/last but not an additional security on top of that unless you have a pet."
And I say this specifically because I believe that's an extremely poor landlord practice, don't want you to do it when you become a landlord, and is not consistent with the market.
If you're taking 2 months worth of cash, half should ALWAYS be the SECURITY DEPOSIT, and specifically state in the lease that the money CANNOT be used for the last month's rent. I believe it's in the standard CAR lease. If they give their 30 days' notice and apply any monies with the owner to the last 30 days while they live there, you have zero deposit.
This puts the ball in the tenant's court. You have to come try to get the money for any cleaning, repairs, etc. Instead of them having an incentive to get their money back rightfully from you. No no no. And don't expect to get that treatment as a tenant. Unless you can find the right sucker. (Robert, no personal offense. But I strongly believe in everything I say above.)
I also have a meetup in Oakland with just fun stuff - totally not related to real estate. I think the name on Meetup is Lake Merritt, Oakland, and Beyond.
Duplex - 4plex for sale in Oakland
I own a duplex in West Oakland with a partner on BP. Wouldn't be insulted by an offer. To really unlock the value of the property, someone needs to owner-occupy the property to utilize the owner-occupant rent control exemption. We do not plan to do so right now. So surprise us ;)
Networking
The Summit is awesome if you can make it and a great way to get introduced to the area and different topics from BP folks all in one weekend. We'll also be having an "investing in the SF Bay" panel with successful local investors making it work in a higher-cost area. Definitely go to the local meetups on BP, and there are some good ones on Meetup too. @Johnson H.'s in Milpitas is my favorite.
@Dan Mackin
Thanks for the shout out, and all your help on the Summit last year! That was amazing!
Rent Control
Yes, there is an issue with your problem to fix, then evict/move, then evict/move. If you're living in a unit in the building, it would be extremely difficult if not impossible to evict an additional unit as an Owner Move-In (OMI). Especially repeatedly. I can barely touch the tip of the iceberg on this, but here's the relevant info:
Here is an (older) summary from legal counsel:
"Once a landlord has recovered possession of a rental unit for either the landlord’s use or the use of a relative, no other unit may be evicted for owner/relative move-in. Any future evictions taking place in the same building for an owner/relative move-in must be on that same unit."
https://www.tobenerlaw.com/oakland-rent-control/
And the city's rules and regs:
http://rapwp.oaklandnet.com/resources/faq/
I'll be in Seattle for the next couple weeks, but hope to meet you in person when I get back or at the Summit :)