A contractor is proposing to do the roofing and siding through my insurance, he says it will save me out of pocket money.

The advantage of CHBO is that they list with lots of other insurance companies and other marketing companies (like homeaway and sublet etc...) that market your property to those looking for monthly, short term rentals.  

He had data on the taxes and insurance.

I want to get my financing within an LLC and it’s very difficult to find a reasonable interest rate.I have worked 25 years to build a modest net worth and will not risk losing it in a frivolous lawsuit by not having the proper legal entity in place that only costs a couple $100 to create and protect my life’s work.People who advise that an insurance policy alone is enough are not necessarily correct in my opinion.

You don't indicate what your loan basis is - but on basis of $125K your Monthly P & I will be around $710 Plus Insurance & Taxes. 

On the notes I hold, I need to make sure the cash comes in and the property tax and insurance are paid.

Although I'm not sure if flood insurance would be covered in HOA fees.

Also, mortgage insurance is expensive! 

While I think there are always deals in every market, I don't think now is the time to jump into the Dallas market.I have walked thru a lot of houses that I think are being offered at nosebleed prices, especially from wholesalers.Be careful with DFW, high property taxes and high property insurance. 

We are closing on our second rental property next week and I was looking for some advice when it comes to a Landlord Insurance Policy.