Everyone else’s rates will look the same way so level playing field.

Don't play around or try to figure it out on your own because that's just as likely to fail or cost you even more.

Their personal income and statements will come into play, but many lenders I work with won't lend to an LLC with more than 2 members on a bank statement or Asset based loan. 

This could be a power play for you, but unlocking the equity and increasing return.I understand turn overs can be a pain, but in a situation like this, there is considerable upside opportunity for you.

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.