I think I have a pretty good handle on many aspects but the biggest unknowns for me are possible  maintenance and repair expenses for the foreseeable future as well as the biggest wild card would be when a tenant might voluntarily move out of a rent controlled unit.  

There too many unknowns in your post. 

Interested Parties may included those who merely have an 'interest' as well as those who are both potential heirs, beneficiaries, creditors and other claimants.You are making a commitment to market to others whose relationship in the big picture could be unknown.

With so many unknowns I almost feel like a fool walking in to the bank inquiring.

If you and the seller can't have a meeting of minds in the middle, great you move onto the next one.FHA on MFR, especially with our older housing stock in the Bay Area, it's a giant unknown if you can even get the property until the appraisal is back.More generally your best bet for using FHA to buy a MFR in the Bay Area will be to go find something off market where you aren't in competition with multiple other buyers putting 30% down, etc.

How long will it take to sell is unknown, but surely there's someone out there looking for a truck like mine.

Hey Shayna,I think everyone can speak to the fear of the unknown.

Whereas title Insurance protects you against unknown, not currently evident problems, that may become known later.  

you are betting your airbnb reputation on so many unknown/uncontrollable variables.

These stories are helping me push through this fear of the unknown.