(S)he should have access to a number of insurers and policy types.I checked with Proper and Steadily and both do not allow more than one booking in a house at the same time.I'm wondering if there are any other insurances that do allow it?

But a couple things to note:What happens to real estate taxes when you pay for 1.45mm?  

No, I said the loan cannot be less than 10 year-term, if I cannot find a 30-year term.Joel Barjon

And, as Nathan noted, you are likely giving up huge appreciation potential, which will likely never be replaced by cash flow.But at the end of the day, if you are in a declining market in LA and are able to find great deals in higher cash flow areas, taking into account the likelihood of needing to outsource everything and additional travel costs to visit the properties a couple times per year, and you don't really care about appreciation, then it could work for you.  

Usually, there is no taxable event if the LLC owners are the same as the current property owner.

I would be taking out more money than the 6% anually from the stocks, but my thinking is that I could make that money last 4-5 years and after those years do another cash out refi and repeat the process.

You are going to 3x your interest rate so more than likely your payment will go up so what you have right now is probably the most affordable and any more borrowing will just increase your payment.

Also I wouldn’t lower the sales price by more than 30-60 days holding cost.   

That will usually suffice. 

My thought was I could purchase the property, break even, and refinance in a couple years when rates hopefully come down.