Prop 10 would just make your already-negative cash flow worse if it pans out as it is anticipated it would.With that said, I own a duplex in Venice and I'm dreading it getting passed.

This is the definition of a paint and carpet rehab and I anticipate about 15k in repairs to get the property ready to sale or about 5k if getting it ready to rent.  

Its cashflowing well like I anticipated.

We anticipate some appreciation over time.

Now, I am nowhere as experienced as some other guys on this forum, but I feel like, if you're always anticipating the markets, you'll always be on the sideline.

I don’t anticipate it being easy for a large family to find another suitable place in just 2 months... any suggestions on how to fairly handle this while still being able to accomplish my goals of having it ready to be viewed in just 4 months? 

It is the engineer's obligation to him or herself as well as the client to anticipate approximately 3 planchecks depending on the complexity of the project.

It really is a national business and you probably want someone with enough band width and experience to anticipate issues and avoid them rather an have an "oops" moment down the road.

Does your $ amt per door also anticipate for these “unexpected” maintenance?

Market an anticipated vacancy.