I have a property in Daly City, less then 5 minutes from SF, which is currently being rented out by a family upstairs and has recently been vacated in the separated downstairs garage area, which currently has a permitted bathroom and (I believe a permitted) bedroom.

No EINs, no separate tax return, and less hassle and expense. 

And furthermore, I believe I have also heard that it advisable to have each rental property set up in separate LLC’s.

Fyi the basement has its own separate entrance and i added a window for the bedroom to be legal.

I forgot that the appraiser had listed my previous property as both a "sold" property from when a bought it and a listed/unsold property from when I rented it as two separate comps.

There is an entire separate court system and set of laws and responsibilities that governs the relationship between a landlord and a tenant.

Usually I don't take roommate rent separately, as it always causes problems, but you are essentially only talking 50% and deferring the rest with no late fee.

Hi Tyler -I've "lived" with couples twice before, once in a conventional house hack situation (I lived in one unit of the building, and they lived in another), and once as "roommates" (separate bedrooms but common kitchen/living room).Wasn't an issue at all in the former.In the latter (which, if I understand correctly, is the situation that you're considering), I had a conversation with them up front about intimacy and inclusivity in common spaces.

I would keep it separate. 

Same as garbage but are the apartments in separate meters?