In my case, I have residential rentals in one LLC, commercial properties in another, self-storage in a third, and my real estate company operates in a fourth.

I have noticed that as companies they grow, their quality and attentiveness tend to decrease. 

There's usually a good reason why a company is cheaper or more expensive.

Since the previous owner is getting most of the proceeds does the closing attorney issue him a 1099S and then issue my company one for a much lower amount?

Then, I spoke with several acquisition managers with very limited knowledge on how to evaluate a deal but this time, the company they were working for was sued by multiple homeowners for fraud.

People have been dropped by insurance companies in wildfire areas and had to scramble to try to find insurance - some using California Fair Plan. 

Yes, they can dispute the charge and then the CC company will have to open a dispute that you will have to answer to attempt to get your money. 

Mine are long term rentals (in 2 states), 3 SFH and 1 mult-unit and they recommended a Wyoming Trust over a Holding Company over an LLC for each property.

Most cost segregation study companies provide the quote for free.

Being a lender for 10 years, all is that we required from the title company and the lender is that a notarized close was to take place.