Considering moving from SFH to house hacking in SF / Bay Area

[Varun M.]

Hello Bay Area house hackers, 

Hope you're doing well. My wife and I currently own a SFH in Sunset, San Francisco. We've been reading up on house hacking and have been considering selling our SFH and buy a duplex / triplex in SF Bay Area so we could live in one, and rent the other unit(s). Typical house hacking stuff. Weather is another consideration for us. As much as we like our home and the Sunset, we wouldn't mind moving to a neighborhood that gets a bit more sun. We would prefer staying in SF, but open to considering other neighborhoods in the peninsula south of Palo Alto. Not considering East Bay at the moment.

On the financial side, we have two goals:

(1) build more equity, faster

(2) not increase our monthly mortgage from what we currently pay (in other words, we are fine paying what we currently pay for our SFH, as long as the rental income covers the incremental mortgage)

I would love to chat with you if you have been through a similar journey, or have thoughts on what to consider in making such a move. A few things we are looking to get insight on:

(1) what do you typically give up moving from a SFH to multi-family? And while I understand it's different for everyone, what mattered most to you if you've done it? Full transparency, my wife is concerned we're going to be "downgrading" substantially.

(2) any thoughts on what are some of the areas outside SF which lend themselves nicely to what we are trying to accomplish?

(3) if we were to pull the trigger on this, we would likely want to do a Section 121 to preserve our equity gains, as much as possible, and pour it back towards the downpayment of the multi-family. Are there other financial considerations we should take into account in doing so? I know the right answer here is to talk to a CPA but looking for someone's perspective who has been through it. 

(4) any other considerations we might be overlooking?

Would appreciate any inputs!

Thanks,

Varun