Then job cuts, stock market correction and in increased caution among tech employees should have contributed to several markets including CA, AZ, TX.

As long as you're self employed with no w2 employees other than a spouse or they have to work under 500 hours annually then you qualify. 

Would my subcontractor be covered for his employees if he paints exterior trim on my Maryland property but his workers comp is effective only in VA?  

Meaning at what point do you hire employees, quit other income streams etc… Is the money coming through cash flow from rental properties or buying and selling… I am 21 and just starting out and this of course is the plan for the next 5-10 years but I want to plan ahead. 

This is what happened to me prior to running my firm when I was a w2 employee.

I just read an article that even In-n-Out is closing one of it's long time locations in Oakland because the crime is too high in the area and it's not safe for their employees.

I am a W2 employee that makes about 70K per year, so this is all new for me.  

I am a w2 employee who makes about 60-70k per year and have always just used TurboTax in the past.  

So, I use Personal Capital to track my net worth (at least those parts of my net worth that can be harnessed in the pursuit of financial freedom - doesn't count retirement accounts, my car, or home equity if I owned a home that wasn't an investment property). 

Best bet is just searching HAR.