If I did this, I would NEVER show my Lenders the proposition (maybe unless the investment was SO superior that it beat even your worst-case projections.) 

@David Floyd insurance and LLC are not a one or other proposition.

And this is why discussing low income properties on here is a losing proposition...But I did see good advice sprinkled within the mass stereotypes.

Given the regulatory pressure Airbnb is under it seems like a risky proposition.

Shelter is one of the basic human needs, hardwired way down in the lizard brainstem.You're showing up after years of allowing him to feed his innate tendency to believe that your place is his permanent home for many years, and at some point you're going to present him with the panic-inducing proposition that this is the end of his housing security -- you're not going to be renewing the lease.Ideally, he'll get over it.

Not saying wages will support the housing prices or that it's even a winning proposition...

I think of your proposition as tempting a Python by helping it wrap itself around me as many times as I can just to see  how many times a Python can be wrapped around me before I can no longer break out of its hold.

@Holly Collins - these are 2 different value propositions here.1. cashflow (aka rent)2. resale valueAgain, I think this depends on what your personal real estate goals are and specifically where the property is located on the peninsula.I personally prefer cashflow value because I think it will far out-weigh any negatives when you go to sell in a few decades.

My occupancy is very high as well, north of 75% (kudos to you at 90-95%) but I think sitting on my laurels might be a dangerous proposition, but as you stated it's hard to justify the time, and certainly the cost.

not a worthwhile proposition.