Regarding the decision to sell vs. rent, as an alternative to selling, did you consider doing a cash-out refinance in order to pull out the equity in excess of what you had into it?

I find that when the coverage is gotten from the excess/specialty markets the coverage is often less and the exclusions more than what you would get in a standard policy.

@Jon Schwartz1) To begin with 3 million FMV in California captures innumerable small business owners standing entirely on its own, but if that weren't bad enough, the valuation standard is actually aggregated across all properties owned so it's not in fact in excess of 3 million per property making it much worse still.2) Commercial properties have a very suspiciously expansive scope in the initiative (the devil is in the details, as is typical, and here as well) thus capturing both mom and pop businesses and in many cases even agriculture.3) Unsurprisingly those proffering the provision have acknowledged it is but a first step, once they get their foot in the door with passage of the initiative they will shoot for full repeal of Prop 13 targeting all real estate owners.4) But you make a really great point, sell it as tax on fat cats (while in reality it's scope will hit many many small businesses) makes it palatable to a largely uninformed electorate and further softens them up for delivery of the really big hammer when they shoot for full repeal of Prop 13.

I realize it's a sellers market but the markups I'm seeing seem excessive.

If I recall correctly, dry funded double closes have been misidentified as mortgage fraud in the past thus leading to excessive concern.

At what point do you think I should I recognize this as excessive maintenance costs?

What is the appropriate amount of Umbrella coverage does one need to ensure adequate/robust (but not excessive) coverage? 

Use that money to to buy about 1.2-1.4MM in investment properties whether it be 3-4 SFH or a MFH (not familiar with the area), and use excess cash for some value add cosmetic work if available.

Excess traffic, the neighbors will complain about all the cars2.

What I choose to do with my "excess time" is give it back to others who are pursuing their own journey to financial independence.