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.

We are a very busy group, but I have no doubts that we can grow the business to the level that we will all be happy with.GOALS:First off, we want to build a business big enough that in the next 5 years, it can replace the income of all of our day jobs.

@Zapata Tate Yes, high level overview, it looks like a good deal.

We are a very busy group, but I have no doubts that we can grow the business to the level that we will all be happy with.GOALS:First off, we want to build a business big enough that in the next 5 years, it can replace the income of all of our day jobs.

But most of the accounting data entry is done by my office manager (who does a ton of other stuff)Some of the higher level accounting is done by me. 

Then compare those numbers to the average occupancy levels in your area in different seasons.I hope this was helpful.