One RE Holding Company. Yes or No? Considering future entities.

[Charlie Romano]

Hi All,

This is my very first question in a forum setting. I appreciate the opportunity and any advise on this topic. 
Based on past questions on this very topic, and answers submitted by many members, it almost always comes down to consult or seek answers/advise from an attorney or a CPA without getting a real clue form the BP community. I have asked several attorneys and my CPA.  In my experience they haven’t been able to clearly answer me. This is most likely because they don’t understand the scope of the question or long term idea. Maybe because I’ve asked the wrong people or I’m not asking the question properly. It could also very well be that I don’t know what I’m talking about (which is also a great possibility, at this point, which I’m very much aware of).  Regardless, I appreciate this opportunity and wish everyone much success in their endeavors. 

So allow me to humbly ask:

Is is better to structure one (1) Real Estate Holding Company (LLC - In my case Delaware — The Parent Company) and structure other individual entities for the actual investment properties, in the state where they are located and be owned by the RE Holding Company (Parent Company)? Or just create individual entities for each property in the state where they are located. 
-Registered Agent in place where ever the individual entity is filed in-. 

The goal is to eventually own multiple investment properties/individual entities-LLC (commercial, non-commercial in various states) and be under one Umbrella Company.

The idea is to have property insurance for each property.  
My thought is to create a Holding Company “Brand” that could be viewed as more sophisticated when purchasing other deals in the future?  Instead of just me.  

My thought is that this will create an extra layer of protection between my home, my family and me personally from any liabilities in case something were to happen in one of the investment property. 

Is it too much? Not necessary?

Is it better?
Will it help obtaining financing/loans in the future?
I wonder if Banks look at it differently- more favorable?

Can I still file my taxes through “pass through” if I’m the single member manger of the RE Holding Company?

How can I accomplish the simplest way to file taxes if it is concluded that it is better to create a holding company.  

Who should be on the title of the individual property entity? Me as the individual? Me as a single member manger LLC of that property or the RE Holding Company which is under my name anyway.

Ultimately I’d like to be in control of my assets but of course I’d like to take advantage of properly structuring it under an LLC and/or a Holding Company. 

Just trying to get an idea of what would be a good way to structure this with a solid foundation to build upon. 

Thank you again and wishing everyone a safe and sound future.  

Charlie