Quote from @Dan Bitner:
@Matt K., I think it makes it tougher, but not impossible. If the property's occupied units are already at or near market value you have a chance. Certainly, if you live it in for a year and then vacate, you can list it at market value. Example: https://www.redfin.com/CA/San-... the occupied 2 bed is at $3200/month and you can probably get $3500 for the second unit. Rent control would be a 2-3% up charge per year so an extra $100/unit/month. Depending on downpayment & purchase price, you could still get some modest cash flow (or at least I hope so)
That unit you linked is going to right near 9k mo to operate, not including any maintenance which these old buildings will need at some point.
so at current rates and situation, you're getting 3200 on side and you'd need 5800 for the other side.
if you bumped up rent on the other side you'd still not get the 4500 you need, you'd be a thousand short.
plus little upside for that property because it's already nice and you're only left with appreciation.
I am not saying your idea is bad, but you did pick a location that makes it almost impossible. From a inventory/rent perspective there's better locations outside of SF.
And again this assumes you're going the low down payment route...