@Michael BaumThe coverages levels and deductibles are very similar.

In an attempt to level out the situation the unintended consequences are going to to be catastrophic.  

The home is a 3 story house with a large separate two-story garage behind it, the garage has a two-bedroom apartment on the top level.

The level of work is different.

Requesting Referrals for an Investor friendly insurance agent in the Baltimore City, Maryland area for a Commercial Liability Umbrella Policy (CLUP).Current portfolio: 8 RentalsBRRRR investor - another question is how the properties (or level of difficulty) will be added/removed to the Umbrella as the properties go in my personal name and then refinanced into the LLC.Bonus question - If refinanced to an LLC, do I still need an umbrella?

High-end finishes throughout, 2 car garage on a huge lot/backyard, large 2nd story loft area, 1st level front porch, 2nd level deck off master and a large deck off the back of the house.

Hi @Dane MacLeod, Usually at the level of doing hundreds of homes business owners are using a mix of both the personal credit and the health of the business. 

I am simply looking to get the roof reshingled (not even sheathing work).The home is in Orange County, NY where there is no license requirement on the county level.

With that in mind general liability insurance appears to be the best option.What would be a good level of protection when starting out (1/2 million)? 

The number of women in mid-level roles, however, has increased 5% during that time.