So what you’re claiming is that Ohio Cashflow creates “false scarcity” because we send generic pre-scheduled marketing emails with properties sold months ago just to showcase examples of what we can offer?

I am aware of a large claim several years ago in Wears Valley where the insurance through VRBO actually paid the claim.

The board of the HOA has reached out to some carriers, but what they're finding is that many large nationwide carriers have a practice of not insuring clients that filed claims in the last three years. 

From a tax perspective, your brother and you both can't claim the interest benefits. 

Then when I did my own research on a few interesting things he talked about, I was unable to find anything to backup his claims.

I was moving forward with them but was just informed i need to sign CA form D-1 which states "the insurer does not patriciate in any of the insurance guarantee funds created by California Law, therefore these funds will not pay your claims or protect your assets if the insurer becomes insolvent" .Seems kind of risky but does anyone have any thoughts on this?

Do I purchase it in the name of the LLC and then quit claim it to the Trust, and, if so, are there any consequences?

Where I live in Lake Tahoe, Nevada there are HOA associations have been poorly run, multiple insurance claims from snow damage, and as a result are increasing fees to cover the low fees of the past and capital expenditures that have been put off for years. 

Could get a policy with it as a second/vacation home, but expect I'd run into claims issues if BnB renters caused a problem.

You could have had claim forgiveness on your policy (for your first claim)3.