I am growing my personal portfolio and my management portfolio but not actively seeking arbitrage deals. 

The question becomes, what if the quality of life degrades to the degree that SF or any other blue city sees a shrinking population (ie Detroit in years past).

In person its a place I could see maybe doing an investment or two in but its not where I really want to set up shop (I mean that literally; set up a home and also set up a wood shop - so I can build custom cabinets and stuff).If Santa Cruz, CA ever goes on sale then I'll go there and suck it up with CA laws and cost of living, but for the foreseeable future it is not even a remotely viable option; I looked at a fourplex there generating $10k in monthly income and priced at $2,700,000. 

An LLC is used to hold business assets.A house-hack is a partial personal property / business property.You also have to separate business and personal assets within an LLC.So the question is would you be getting the protection that you are looking for by putting an asset that is partially personal within an LLC.You might also be losing your homestead exemption.Best of luck.

So what your telling me is you would not take the advice of some random stranger to make the biggest financial decision of your life? 

Initially we were set on purchasing a Primary Residence again, single family or townhome within reach of my sons school and continuing life as usual, but feel like we are slightly priced out of the market we want and areas we need to live. 

Since I am converting my Primary Residences into a STR MID-YEAR, does that go beyond the personal use days or does it start counting after STR service starts? 

Arbitrage is not looked upon fondly here.Speaking personally, if I were a property owner with a rental and you said you wanted to do a STR with it, I would not be interested. 

They then decide one day to sell and throw these ridiculously low maintanance costs out on their proformas not understanding how they sucked the life out of their assets. 

This home was built for an investor and next to a personal build I kept for myself.