This is where the relationship part of the process comes in to play. 

If your roof is $10,000 to replace, then you could actually come out ahead.Each claim and investor situation is unique and plays out differently.

My understanding is that it will play out over the next few decades.

While I have the knowledge, I do not have the connections needed to play the game.

My understanding is that California has yearly $800 fees for LLCs, so likely I would put my 3 properties into a single LLC as opposed to playing $2400 per year to maintain, Should I then look at an umbrella policy for the LLC to additionally cover all 3?

As a buyer, If you asked me to sign a non-disclosure or show proof of funds, I guess that would be fine IF there was an actual deal in play.

Whenever people get ready to sell they want the highest NOI, so they limit their expenses, This where your due diligence comes into play.

Now there is a whole lot more at play.

Lower Westchester is tough to make cashflow in on a house hack but is always a good long-term equity and appreciation play!

I don't think I'm gonna work when I have a personal golf course that needs to be played on!"